Skip to main content
SpringerLink
Log in

β-Lactam Ring Opening: A Useful Entry to Amino Acids and Relevant Nitrogen-Containing Compounds

  • Chapter
  • First Online:
Book cover Heterocyclic Scaffolds I

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 22))

Abstract

The main strategies for the ring opening of β-lactams by chemical means are described. The discovery of each approach is put into context, sometimes in connection to processes occurring in biological systems, and the synthetic opportunities each approach offers are shown. Thus, this β-lactam route affords a number of synthetically relevant building-blocks, including α-amino acids, β-amino acids, their derived peptides, and other nitrogen containing heterocycles and open chain molecules. The content, which encompases references to initial work, further major development, and the most relevant recent literature contributions, is categorized according to the ring bond cleavaged (N 1–C 2, C 2–C 3, C 3 –C 4 , N 1–C 4), to finish with ring opening strategies leading to large heterocyclic compounds. Within each category, distinction has been made according to the type of nucleophilic agent employed, principally O-, N-, and C-nucleophiles. Also, a variety of applications of the strategy to the synthesis of interesting target compounds are shown.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

Ac:

Acetyl

AcOH:

Acetic acid

AD:

Asymmetric dihydroxylation

Ar:

Aryl

Bn:

Benzyl

Boc:

tert-butoxycarbonyl

Bu:

Butyl

Bz:

Benzoyl

CAN:

Ceric ammonium nitrate

Cbz:

Benzyloxycarbonyl

cHex:

Cyclohexyl

CSA:

Camphorsulfonic acid

DCC:

N,N-dicyclohexylcarbodiimide

DIBAL:

Lithium diisobutylaluminium hydride

DMAP:

4-(dimethylamino)pyridine

DMD:

Dimethyldioxirane

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

Et:

Ethyl

Fmoc:

9-fluorenylmethoxycarbonyl

Gly:

Glycine (glycinyl)

HMDS:

Hexamethyldisilazide

HMPA:

Hexamethylphosphoric triamide

HOBt:

N-hydroxyl benzotriazole

LDA:

Lithium diisopropylamide

Leu:

Leucine (leucinyl)

LHMDS:

Lithium hexamethyldisilazide

mCPBA:

3-chloroperoxybenzoic acid

Me:

Methyl

MS:

Molecular sieves

NCA:

N-carboxy anhydride

NDC:

Nicotinium dichromate

NMM:

N-methyl morpholine

Nu:

Nucleophile

PDC:

Pyridinium dichromate

Ph:

Phenyl

Phe:

Phenylalanine (phenylalaninyl)

PMP:

4-(methoxy)phenyl

Pr:

Propyl

p-Tos:

4-(methylphenyl)sulfonyl

p-Tolyl:

4-methylphenyl

SEM:

2-(trimethylsilyl)ethoxymethyl

Succ:

Succinyl

TBAF:

Tetrabutylammonium fluoride

TBDPS:

tert-butyldiphenylsilyl

TBS:

tert-butyldimethylsilyl

TEMPO:

2,2,6,6-tetramethylpiperidinyl-1-oxyl

TES:

Triethylsilyl

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

Thz:

2-thiazolyl

TIPS:

Triisopropylsilyl

TMS:

Trimethylsilyl

TMSOTf:

Trimethylsilyl trifluoromethanesulfonate

UV:

Ultraviolet

Val:

Valine (valinyl)

References

  1. Clark HT, Jonson JR, Robindon R (1949) The chemistry of penicillins. Princeton University Press, New Jersey

    Google Scholar 

  2. Morin RB, Goldman M (1982) (eds) Chemistry and biology of β-lactam antibiotics, vol. 1–3. Academic Press, New York

    Google Scholar 

  3. Demain AL, Solomon NA (1983) (eds) Antibiotics containing the β-lactam structure, parts 1&2. Springer, Berlin

    Google Scholar 

  4. Bentley PH, Ponsford R (1993) (eds) Recent advances in the chemistry of anti-infective agents. The Royal Society of Chemistry, Cambridge

    Google Scholar 

  5. Niccolai P, Tarsi L, Thomas RJ (1997) Chem Commun 2333

    Google Scholar 

  6. Bronson JJ, Barrett JF (2001) Curr Med Chem 8:1775

    CAS  Google Scholar 

  7. Edwards PD, Bernstein PR (1994) Med Res Rev 14:127

    CAS  Google Scholar 

  8. Mascaretti OA, Boschetti CE, Danelo GO, Mata EG, Roveri OA (1995) Curr Med Chem 1:441

    CAS  Google Scholar 

  9. Wilmouth RC, Kasamally S, Westwood NJ, Sheppard RJ, Claridge TD, Alpin PA, Wright PA, Pritchard GJ, Schofield CJ (1998) Biochemistry 38:7989

    Google Scholar 

  10. Burnett DA (2004) Curr Med Chem 11:1873

    CAS  Google Scholar 

  11. Bruggink A (2001) Synthesis of β–lactam antibiotics. Kluver, Dordecht (The Netherlands)

    Google Scholar 

  12. Page MI (1992) (ed) The chemistry of β-lactams. Chapman and Hall, London

    Google Scholar 

  13. Georg GI (1993) (ed) The organic chemistry of β-lactams. VCH, New York

    Google Scholar 

  14. Kidwai M, Sapra P, Bhushan KR (1999) Curr Med Chem 6:195

    CAS  Google Scholar 

  15. Koppel GA (1983) In: Hasnner A (ed) Small ring heterocycles, vol. 42. Wiley, New York, p 219

    Google Scholar 

  16. Backes J (1991) In: Muller E, Bayer O (eds) Houben-Weyl, Methoden der Organischen Chemie, band E16B. Thieme, Stuttgart, p 31

    Google Scholar 

  17. De Kimpe N (1996) In: Katrizky AR, Rees CW, Scriven EFV, Padwa A (eds) Comprehensive heterocyclic chemistry II, vol. 1B. Pergamon, Oxford, p 507

    Google Scholar 

  18. Singh GS (2003) Tetrahedron 59:7631

    CAS  Google Scholar 

  19. Gómez-Gallego M, Manchego MJ, Sierra MA (2000) Tetrahedron 56:5743

    Google Scholar 

  20. Alcaide B, Almendros P (2002) Curr Org Chem 6:1

    Google Scholar 

  21. Staudinger H (1907) Liebigs Ann Chem 356:51

    CAS  Google Scholar 

  22. Van der Steen FH, Van Koten G (1991) Tetrahedron 47:7503

    Google Scholar 

  23. Georg GI, Ravikumar VT (1993) The organic chemistry of β–lactams. VCH, New York, p 295

    Google Scholar 

  24. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (1999) Eur J Org Chem 3223

    Google Scholar 

  25. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (2004) Curr Med Chem 11:1837

    CAS  Google Scholar 

  26. Hart DJ, Ha DC (1989) Chem Rev 89:1447

    CAS  Google Scholar 

  27. Brown MJ (1989) Heterocycles 29:2225

    CAS  Google Scholar 

  28. Georg GI (1989) In: Atta-ur-Rahman (ed) Natural product chemistry, vol 4. Elsevier, Amsterdam, p 431

    Google Scholar 

  29. Cainelli G, Panunzio M, Andreoli P, Martelli G, Spunta G, Giacomini D, Bandini E (1990) Pure Appl Chem 62:605

    CAS  Google Scholar 

  30. Cainelli G, Panunzio M, Giacomini D, Martelli G, Spunta G, Bandini E (1996) In: Chatgilialoglu C, Snieckus V (eds) Chemical synthesis, gnosis to prognosis. Kluwer, Amsterdam, p 25

    Google Scholar 

  31. Fujisawa T, Shimizu M (1996) Rev Heteroatom Chem 15:203

    CAS  Google Scholar 

  32. Benaglia M, Cinquini M, Cozzi F (2000) Eur J Org Chem 563

    Google Scholar 

  33. Miller MJ (1986) Acc Chem Res 19:49

    CAS  Google Scholar 

  34. Chmielewski M, Kaluza Z, Forman B (1996) Chem Commun 2689

    Google Scholar 

  35. Kinugasa M, Hashimoto SJ (1972) Chem Soc Chem Commun 466

    Google Scholar 

  36. Miura M, Enna M, Okuro K, Nomura M (1995) J Org Chem 60:4999

    CAS  Google Scholar 

  37. Lo MM-C, Fu GC (2002) J Am Chem Soc 124:4572

    Google Scholar 

  38. Shintani R, Fu GC (2003) Angew Chem Int Ed 42:4082

    CAS  Google Scholar 

  39. Basak A, Ghosh SC, Bhowmick T, Das AK, Bertolasi V (2002) Tetrahedron Lett 43:5499

    CAS  Google Scholar 

  40. Marco-Contelles J (2004) Angew Chem Int Ed 43:2198

    CAS  Google Scholar 

  41. Mascaretti OA, Boschetti CE, Danelon GO, Mata EG, Roveri OA (1995) Curr Med Chem 1:441

    CAS  Google Scholar 

  42. Page MI, Laws AP (1998) Chem Commun 1609

    Google Scholar 

  43. Fisher JF, Meroueh SO, Mobashery S (2005) Chem Rev 105:395

    CAS  Google Scholar 

  44. Tsang WY, Ahmed N, Hinchliffe PS, Wood JR, Harding LP, Laws AP, Page MI (2005) J Am Chem Soc 127:17556

    CAS  Google Scholar 

  45. Crowder MW, Spencer J, Vila AJ (2006) Acc Chem Res 39:721

    CAS  Google Scholar 

  46. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (2000) Pure Appl Chem 72:1763

    CAS  Google Scholar 

  47. Forró E, Fülöp F (2004) Mini-Rev Org Chem 1:93

    Google Scholar 

  48. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (2001) Synlett 1813

    Google Scholar 

  49. Palomo C, Aizpurua JM, Ganboa I (1997) In: Juaristi E (ed) Enantioselective synthesis of β-amino acids. Wiley-VCH, New York, p 279

    Google Scholar 

  50. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M (2005) In: Juaristi E, Soloshonok V (eds) Enantioselective synthesis of β-amino acids, 2nd edn. Wiley-VCH, Hoboken, NJ, p 477

    Google Scholar 

  51. Alcaide B, Almendros P (2002) Synlett 381

    Google Scholar 

  52. Forró E, Fülöp F (2006) Tetrahedron Asymmetry 17:3193

    Google Scholar 

  53. For a recent mechanistic study, see Dal Peraro M, Vila AJ, Carloni P, Klein ML (2007) J Am Chem Soc 129:2808

    Google Scholar 

  54. Fernández-Suárez M, Muñoz L, Fernández R, Riguera R (1997) Tetrahedron Asymmetry 8:1847

    Google Scholar 

  55. Shirode NM, Rakkeb A, Deshmukh AS (2006) Tetrahedron 62:4615

    CAS  Google Scholar 

  56. Alcaide B, Almendros P (2001) Chem Soc Rev 30:226

    CAS  Google Scholar 

  57. Kale AS, Rakeeb A, Deshmukh AS (2005) Synlett 2370

    Google Scholar 

  58. Gyarmanti ZC, Liljeblad A, Argay G, Kálmán A, Bernáth G, Kanerva LT (2004) Adv Synth Catal 346:566

    Google Scholar 

  59. Sierra MA, Pellico D, Gómez-Gallego M, Manchego MJ, Torres R (2006) J Org Chem 71:8787

    CAS  Google Scholar 

  60. Palomo C, Arrieta A, Cossío FP, Aizpurua JM, Mielgo A, Aurrekoetxea N (1990) Tetrahedron Lett 31:6429

    CAS  Google Scholar 

  61. Palomo C, Aizpurua JM, Urchegui R, Iturburu M (1992) J Org Chem 57:1571

    CAS  Google Scholar 

  62. Mishra RK, Coates CM, Revell KD, Turos E (2007) Org Lett 9:575

    CAS  Google Scholar 

  63. Sathe M, Ghorpade R, Kaushik MP (2006) Chem Lett 35:1004

    CAS  Google Scholar 

  64. Pfeiffer B, Peduzzi E, Moehle K, Zurbriggen R, Glück R, Pluschke G, Robinson JA (2003) Angew Chem Int Ed 42:2368

    CAS  Google Scholar 

  65. Hogan PC, Corey EJ (2005) J Am Chem Soc 127:15386

    CAS  Google Scholar 

  66. De Vitis L, Troisi L, Granito C, Pindinelli E, Ronzini L (2007) Eur J Org Chem 356

    Google Scholar 

  67. Flynn DL, Zelle RE, Grieco PA (1983) J Org Chem 48:2424

    CAS  Google Scholar 

  68. Coantic S, Mouysset D, Mignani S, Tabart M, Stella M (2007) Tetrahedron 63:3205

    CAS  Google Scholar 

  69. Holton RA (1990) Eur Pat Appl EP400, 971; Chem Abstr 114:164568q

    Google Scholar 

  70. Holton RA, Liu JH (1993) Bioorg Chem Lett 3:2475

    CAS  Google Scholar 

  71. Ojima I, Habus I, Zhao M, Zucco M, Park YH, Sun CM, Brigaud T (1992) Tetrahedron 48:6985

    CAS  Google Scholar 

  72. Nicolaou KC, Dai W-M, Guy RK (1994) Angew Chem Int Ed Engl 33:15

    Google Scholar 

  73. Kingston DGI (2001) Chem Commun 867

    Google Scholar 

  74. Ge H, Spletstoser JT, Yang Y, Kayser M, Georg GI (2007) J Org Chem 72:756

    CAS  Google Scholar 

  75. Palomo C, Aizpurua JM, Cuevas C, Mielgo A, Galarza R (1995) Tetrahedron Lett 36:9027

    CAS  Google Scholar 

  76. Alonso E, Pozo CD, Gozález J (2002) Synlett 69

    Google Scholar 

  77. Chen A, Nelson A, Tanikkul N, Thomas EJ (2001) Tetrahedron Lett 42:1251

    CAS  Google Scholar 

  78. Romo D, Rzasa RM, Shea HA, Park K, Langenhan JM, Sun L, Akhiezer A, Liu JO (1998) J Am Chem Soc 120:12237

    CAS  Google Scholar 

  79. Eggen MJ, Nair SK, Georg GI (2001) Org Lett 3:1813

    CAS  Google Scholar 

  80. Vidya R, Eggen MJ, Nair SK, Georg GI, Himes RH (2003) J Org Chem 68:9687

    CAS  Google Scholar 

  81. Dondoni A, Massi A, Sabbatini S, Bertolasi V (2004) Adv Synth Catal 346:1355

    CAS  Google Scholar 

  82. Cardillo G, Tomasini C (1996) Chem Soc Rev 23:117

    Google Scholar 

  83. Juaristi E, López-Ruiz H (1999) Curr Med Chem 6:983

    CAS  Google Scholar 

  84. von Nussbaun F, Anlauf S, Benet-Buchholz J, Häbich D, Köbberling J, Musza L, Telser J, Rübsamen-Waigmann H, Brunner NA (2007) Structure corroboration and total synthesis. Angew Chem Int Ed 46:2039

    Google Scholar 

  85. Palomo C, Aizpurua JM, Ganboa I, Odriozola B, Maneiro E, Miranda JI, Urchegui R (1996) Chem Commun 161

    Google Scholar 

  86. Tsang WY, Ahme N, Page MI (2007) Org Biomol Chem 5:485

    CAS  Google Scholar 

  87. Palomo C, Aizpurua JM, Cuevas C (1994) J Chem Soc Chem Commun 1957

    Google Scholar 

  88. Ojima I, Sun CM, Park YH (1994) J Org Chem 59:1249

    CAS  Google Scholar 

  89. Palomo C, Aizpurua JM, Galarza R, Mielgo A (1996) Chem Commun 633.

    Google Scholar 

  90. Palomo C, Aizpurua JM, Galarza R, Benito A, Khamrai UK, Eikeseth U, Linden A (2000) Tetrahedron 56:5563

    CAS  Google Scholar 

  91. Palomo C, Oiarbide M, Bindi S (1998) J Org Chem 63:2469

    CAS  Google Scholar 

  92. Durham TB, Miller MJ (2003) J Org Chem 68:35

    CAS  Google Scholar 

  93. Cundy DJ, Donohue AC, McCarthy TD (1998) Tetrahedron Lett 39:5125

    CAS  Google Scholar 

  94. Cundy DJ, Donohue AC, McCarthy TD (1999) J Chem Soc Perkin Trans 559

    Google Scholar 

  95. Khim S-K, Nuss JM (1999) Tetrahedron Lett 40:1827

    CAS  Google Scholar 

  96. Jiang X, Prasad K, Prasad M, Slade J, Repič O, Blacklock TJ (2006) Synlett 3179

    Google Scholar 

  97. Baldwin JE, Adlington RM, Rusell AT, Smith ML (1995) Tetrahedron 51:4733

    CAS  Google Scholar 

  98. Nakamura T, Shiozaki M (1999) Tetrahedron Lett 40:9063

    CAS  Google Scholar 

  99. Nakamura T, Shiozaki M (2001) Tetrahedron 57:9087

    CAS  Google Scholar 

  100. Palomo C, Aizpurua JM, García JM, Iturburu M, Odriozola JM (1994) J Org Chem 59:5184

    CAS  Google Scholar 

  101. Palomo C, Aizpurua JM, Gracenea JJ (1999) J Org Chem 64:1693

    CAS  Google Scholar 

  102. Spero DM, Kapadia S, Farina V (1995) Tetrahedron Lett 36:4543

    CAS  Google Scholar 

  103. Ojima I, Ng EW, Sun CM (1995) Tetrahedron Lett 36:4547

    CAS  Google Scholar 

  104. Westermann B, Walter A, Diedrichs N (1999) Angew Chem Int Ed 38:3384

    CAS  Google Scholar 

  105. Ha D-C, Kang S, Chung C-M, Lim H-K (1998) Tetrahedron Lett 39:7541

    CAS  Google Scholar 

  106. Parsons PJ, Camp NP, Underwood JM, Harvey DM (1996) Tetrahedron Lett 52:11637

    CAS  Google Scholar 

  107. Lee HK, Chun JS, Pak CS (2003) J Org Chem 68:2471

    CAS  Google Scholar 

  108. Lee HK, Chun JS, Pak CS (2001) Tetrahedron Lett 42:3483

    CAS  Google Scholar 

  109. Lee HK, Chun JS, Pak CS (2003) Tetrahedron 59:6445

    CAS  Google Scholar 

  110. Birch NJ, Parsons PJ, Scopes DIC (2004) Synlett 2776

    Google Scholar 

  111. Krämer B, Franz T, Picasso S, Pruschek P, Jäger V (1997) Synlett 2776

    Google Scholar 

  112. Ojima I, Zhao M, Yamato T, Nakahashi K, Yamashita M, Abe R (1991) J Org Chem 56:5263

    CAS  Google Scholar 

  113. Baldwin JE, Adlington RM, Elend AS, Smith ML (1995) Tetrahedron 51:11581

    CAS  Google Scholar 

  114. Buttero PD, Molteni G, Roncoroni M (2006) Tetrahedron Lett 47:2209

    Google Scholar 

  115. Alcaide B, Almendros P, Cabrero G, Ruiz MP (2007) J Org Chem 72:7980

    CAS  Google Scholar 

  116. Palomo C, Aizpurua JM, Miranda JI, Mielgo A, Odriozola JM (1993) Tetrahedron Lett 34:6325

    CAS  Google Scholar 

  117. Alcaide B, Almendros P (2001) Org Prep Proc Int 33:315

    Google Scholar 

  118. Palomo C, Aizpurua JM, Ganboa I, Carreaux F, Cuevas C, Maneiro E, Ontoria JM (1994) J Org Chem 59:3123

    CAS  Google Scholar 

  119. Alcaide B, Almendros P, Aragonzillo C (2000) Chem Commun 757

    Google Scholar 

  120. Alcaide B, Almendros P, Aragoncillo C (2002) Chem Eur J 8:3646

    CAS  Google Scholar 

  121. Kricheldorf HR (1987) α-Amino acid N-carboxy-anhydrides and related heterocycles. Springer-Verlag, Berlin

    Google Scholar 

  122. Palomo C, Aizpurua JM, Cuevas C, Urchegui R, Linden A (1996) J Org Chem 61:4400

    CAS  Google Scholar 

  123. Palomo C, Oiarbide M, Esnal A (1997) Chem Commun 691

    Google Scholar 

  124. Palomo C, Oiarbide M, Esnal A, Landa A, Miranda JI, Linden A (1998) J Org Chem 63:5838

    CAS  Google Scholar 

  125. Coppola GM, Schuster HF (1997) α-Hydroxy acids in enantioselective synthesis. VCH, Wienheim

    Google Scholar 

  126. Gawronski J, Gawronska K (1999) Tartaric and malic acids in synthesis. Wiley, New York

    Google Scholar 

  127. Ghosh AK, Koltun ES, Bilcer G (2001) Synthesis 1281

    Google Scholar 

  128. Kolb HC, Van Nieuwenhze MS, Sharpless KB (1994) Chem Rev 94:2483

    CAS  Google Scholar 

  129. Palomo C, Oiarbide M, Landa A (2000) J Org Chem 65:41

    CAS  Google Scholar 

  130. Palomo C, Oiarbide M, Landa A, Esnal A, Linden A (2001) J Org Chem 66:4180

    CAS  Google Scholar 

  131. Sim TB, Rapoport H (1999) J Org Chem 64:2532

    CAS  Google Scholar 

  132. Durham TB, Miller MJ (2003) J Org Chem 68:27

    CAS  Google Scholar 

  133. Palomo C, Aizpurua JM, Ganboa I, Maneiro E, Odriozola B (1994) J Chem Soc Chem Commun 1505

    Google Scholar 

  134. Palomo C, Cossío FP, Cuevas C, Lecea B, Mielgo A, Román P, Luque A, Martínez-Ripoll M (1992) J Am Chem Soc 114:9360

    CAS  Google Scholar 

  135. Palomo C, Ganboa I, Cuevas C, Boschetti C, Linden A (1997) Tetrahedron Lett 38:4643

    CAS  Google Scholar 

  136. Palomo C, Aizpurua JM, Urchegui R, García JM (1995) J Chem Soc Chem Commun 2327

    Google Scholar 

  137. Palomo C, Aizpurua JM, Ganboa I, Odriozola B, Urchegui R, Görls H (1996) Chem Commun 1269

    Google Scholar 

  138. Alcaide B, Rodríguez-Ranera C, Rodríguez-Vicente A (2001) Tetrahedron Lett 42:3081

    CAS  Google Scholar 

  139. Macías A, Alonso E, del Pozo C, González J (2004) Tetrahedron Lett 45:4657

    Google Scholar 

  140. Alcaide B, Almendros P, Cabrero G, Ruiz P (2008) Chem Commun 615

    Google Scholar 

  141. Alcaide B, Almendros P, Cabrero G, Ruiz P (2008) Synthesis 2835

    Google Scholar 

  142. Van Brabandt W, De Kimpe N (2005) J Org Chem 70:3369

    Google Scholar 

  143. Van Brabandt W, De Kimpe N (2005) J Org Chem 70:8717

    Google Scholar 

  144. Dekeukeleire S, D’hooghe M, De Kimpe N (2009) J Org Chem 74:1644

    CAS  Google Scholar 

  145. Ojima I, Delaloge F (1997) Chem Soc Rev 26:377

    CAS  Google Scholar 

  146. Ojima I (1995) Adv Asymm Synth 1:95

    CAS  Google Scholar 

  147. Ojima I (1995) Acc Chem Res 28:283

    Google Scholar 

  148. Ojima I (1993) The organic chemistry of β–lactams. Georg GI (ed), VCH, New York, p 197

    Google Scholar 

  149. Ojima I, Komata T, Qiu X (1990) J Am Chem Soc 112:770

    CAS  Google Scholar 

  150. Park J-H, Ha JR, Oh S-J, Kim J-A, Shin D-S, Won TJ, Lam Y-F, Ahn C (2005) Tetrahedron Lett 46:1755

    CAS  Google Scholar 

  151. Mandal PK, Cabell LA, McMurray JS (2005) Tetrahedron Lett 46:3715

    CAS  Google Scholar 

  152. Alcaide B, Almendros P, Redondo MC (2004) Org Lett 6:1765

    CAS  Google Scholar 

  153. Alcaide B, Almendros P, Cabrero G, Ruiz P (2007) Chem Commun 4788

    Google Scholar 

  154. Li G-Q, Li Y, Dai L-X, You S-L (2007) Org Lett 9:3519

    CAS  Google Scholar 

  155. Manhas MS, Amin SG, Bose AK (1976) Heterocycles 5:669

    CAS  Google Scholar 

  156. Manhas MS, Wagle DR, Chiang J, Bose AK (1988) Heterocycles 27:1755

    CAS  Google Scholar 

  157. Deshmukh ARAS, Bhawal BH, Krishnaswamy D, Govande VV, Sinkre BA, Jayanthi A (2004) Curr Med Chem 11:1889

    CAS  Google Scholar 

  158. Alcaide B, Almendros P (2004) Curr Med Chem 11:1921

    CAS  Google Scholar 

  159. Saragovi HU, Fitxpatrick D, Raktabur H, Nakanishi M, Kahn M, Greene MI (1991) Science 253:792

    CAS  Google Scholar 

  160. Williams WV, Kieber-Emmons T, VonFeldt J, Greene MI, Weiner DB (1991) J Biol Chem 266:5182

    CAS  Google Scholar 

  161. Kahn M (1993) Synlett 821

    Google Scholar 

  162. Gardner B, Nakanishi H, Kahn M (1993) Tetrahedron 49:3433

    CAS  Google Scholar 

  163. Wasserman HH (1987) Aldrichim Acta 20:63

    CAS  Google Scholar 

  164. Hesse M (1991) Ring enlargement in organic chemistry. Weinheim, VCH

    Google Scholar 

  165. Ensch C, Hesse M (2002) Helv Chim Acta 85:1659

    CAS  Google Scholar 

  166. Wasserman HH, Matsuyama H, Robinson RP (2002) Tetrahedron 58:7177

    CAS  Google Scholar 

  167. Begley MJ, Crombie L, Haigh D, Jones RCF, Osborne S, Webster RAB (1993) J Chem Soc Chem Commun 2027

    Google Scholar 

  168. Crombie L, Haigh D, Jones RCF, Mat-Zin R (1993) J Chem Soc Chem Commun 2047

    Google Scholar 

  169. Crombie L, Haigh D, Jones RCF, Mat-Zin R (1993) J Chem Soc Chem Commun 2055

    Google Scholar 

  170. De Clerq E, Yamamoto N, Pauwels R, Baba M. Schols D, Nakashima H, Balzarini J, Debyser Z, Murrer BA, Schwartz D, Thornton D, Bridger G, Fricker S, Henson G, Abrams M, Pickers D (1995) Proc Natl Acad Sci 117:3368

    Google Scholar 

  171. Betschart C, Hegedus LS (1992) J Am Chem Soc 114:5010

    CAS  Google Scholar 

  172. Dumas S, Lastra E, Hegedus LS (1995) J Am Chem Soc 117:3368

    CAS  Google Scholar 

  173. Banfi L, Guanti G, Rasparini M (2003) Eur J Org Chem 1319

    Google Scholar 

Download references

Acknowledgements

We thank the following institutions for financial support of our β-lactam program: Ministerio de Educación y Ciencia (Spanish Government), Eusko Jaurlaritza (Basque Government), Euskal Herriko Unibertsitatea-Universidad del País Vasco (University of the Basque Country), and Diputación Foral de Gipuzkoa. All team members cited within the references are also acknowledged.

Author information

Authors and Affiliations

  1. Departamento de Química Orgánica I, Facultad de Química, Universidad del País Vasco, Apdo. 1072, 20080, San Sebastián, Spain

    C. Palomo & M. Oiarbide

Authors
  1. C. Palomo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Oiarbide
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C. Palomo .

Editor information

Editors and Affiliations

  1. Dept. Chemistry, University of Texas-Pan American, W. University Drive 1201, Edinburg, 78539, USA

    Bimal K. Banik

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Palomo, C., Oiarbide, M. (2010). β-Lactam Ring Opening: A Useful Entry to Amino Acids and Relevant Nitrogen-Containing Compounds. In: Banik, B. (eds) Heterocyclic Scaffolds I. Topics in Heterocyclic Chemistry, vol 22. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_11

Download citation

Publish with us

Policies and ethics

Search

Navigation