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N-sulfonyl imines — Useful synthons in stereoselective organic synthesis

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Stereoselective Heterocyclic Synthesis II

Part of the book series: Topics in Current Chemistry ((4143,volume 190))

Abstract

Until recently, N-sulfonyl imines had found only limited and sporadic use in organic synthesis. During the past decade, however, it has become increasingly clear that these species are valuable synthons and are capable of undergoing many unique transformations. A comprehensive review of the chemistry of these compounds is presented here with particular emphasis on their applications in stereoselective processes. Methods for preparing N-sulfonyl imines are outlined, along with a survey of their uses in a wide range of addition, pericyclic and cycloaddition reactions.

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References

  1. For some reviews of the chemistry of N-acyl imines, see Zaug, HE (1982) Synthesis 85, 181

    Google Scholar 

  2. For some reviews of the chemistry of N-acyl imines, Hiemstra H, Speckamp WN (1991) Additions to N-acyl iminium ions. In: Trost BM, Fleming I (eds) Comprehensive Organic Synthesis, Pergamon, Oxford, Vol 2, p 1047

    Google Scholar 

  3. For some reviews of the chemistry of N-acyl imines, Scola PM, Weinreb SM (1989) Chem Rev 89:1525

    Article  Google Scholar 

  4. For some reviews of the chemistry of N-acyl imines, Boger DL, Weinreb SM (1987) Hetero Diels-Alder methodology in organic synthesis, Academic Press, Orlando, Chap 2

    Google Scholar 

  5. For some reviews of the chemistry of N-acyl imines, Malassa I, Matthies D (1987) Chem-Ztg 111: 181, 253

    CAS  Google Scholar 

  6. Lichtenberger J, Fleury J-P, Baretta B (1955) Bull Soc Chim Fr 669

    Google Scholar 

  7. Kretow AJ, Abrazhanova EA (1957) J Gen Chem USSR (Engl Trans) 27:1993

    Google Scholar 

  8. Jennings WB, Lovely CJ (1988) Tetrahedron Lett 29:3725

    Article  CAS  Google Scholar 

  9. Jennings WB, Lovely CJ (1991) Tetrahedron 47:5561

    Article  CAS  Google Scholar 

  10. Davis FA, Zhou P, Lal GS (1990) Tetrahedron Lett 31:1653

    Article  CAS  Google Scholar 

  11. Vishwakarma LC, Stringer OD, Davis FA (1987) Org Synth 66:203

    Google Scholar 

  12. Albrecht R, Kresze G, Mlakar B (1964) Chem Ber 97:483

    Article  CAS  Google Scholar 

  13. Albrecht R, Kresze G (1965) ibid 98:1431

    Article  CAS  Google Scholar 

  14. For a review of N-sulfinyl compounds, see Bussas R, Kresze G, Munsterer H, Schwobel A (1983) Sulfur Rep 2:215

    CAS  Google Scholar 

  15. Hori T, Singer SP, Sharpless KB (1978) J Org Chem 43:1456

    Article  CAS  Google Scholar 

  16. A report exists of the isolation of heterocycles like 2; Pozdnyakova TM, Sergeyev NM, Gorodetskaya NI, Zefirov NS (1972) Int J Sulfur Chem 2:109

    Google Scholar 

  17. Melnick MJ, Freyer AJ, Weinreb SM (1988) Tetrahedron Lett 29:3891

    Article  CAS  Google Scholar 

  18. Sisko J, Weinreb SM (1989) Tetrahedron Lett 30:3037

    Article  CAS  Google Scholar 

  19. Sisko J, Weinreb SM (1990) J Org Chem 55:393 see also Hegedus LS, Holden MS (1986) ibid 51:1171

    Article  CAS  Google Scholar 

  20. Alexander MD, Anderson RE, Sisko J, Weinreb SM (1990) J Org Chem 55:2563 see also Hegedus LS, McKearin JM (1982) J Am Chem Soc 104:2444

    Article  CAS  Google Scholar 

  21. Ralbovsky, JL, Kinsella MA, Sisko J, Weinreb SM (1990) Synth Commun 20:573

    Article  CAS  Google Scholar 

  22. Zhu, S-Z, Chen Q-Y (1991) J Chem Soc Chem Commun 732

    Google Scholar 

  23. Trost BM, Marrs C (1991) J Org Chem 56:6468

    Article  CAS  Google Scholar 

  24. Brown C, Hudson RF, Record KAF (1978) J Chem Soc, Perkin Trans 2 822 and references cited therein

    Google Scholar 

  25. Boger DL, Kasper AM (1989) J Am Chem Soc 111:1517

    Article  CAS  Google Scholar 

  26. Boger DL, Corbett WL, Curran TT, Kasper AM (1991) J Am Chem Soc 113:1713

    Article  CAS  Google Scholar 

  27. Boger DL, Corbett WL (1992) J Org Chem 57:4777

    Article  CAS  Google Scholar 

  28. Barton DHR, Jaszberenyi JC, Theodorakis EA (1991) Tetrahedron 47:9167

    Article  CAS  Google Scholar 

  29. Pickard PL, Tolbert TL (1961) J Org Chem 26:4886

    Article  CAS  Google Scholar 

  30. Georg GI, Harriman GCB, Peterson SA (1995) J Org Chem 60:7366

    Article  CAS  Google Scholar 

  31. Hart DJ, Kanai K, Thomas DG, Yang T-K (1983) J Org Chem 48:289

    Article  CAS  Google Scholar 

  32. Shono T, Matsumura Y, Katoh S, Takeuchi K, Sasaki K, Kamada T, Shimizu R (1990) J Am Chem Soc 112:2368

    Article  CAS  Google Scholar 

  33. Shono T, Matsumura Y, Uchida K, Nakatani F (1988) Bull Soc Chem Jpn 61:3029

    Article  CAS  Google Scholar 

  34. Ross, SD, Finkelstein M, Rudd EJ (1972) J Org Chem 37:2387

    Article  CAS  Google Scholar 

  35. Han G, Weinreb SM, unpublished results

    Google Scholar 

  36. Pines SH, Purick RM, Reamer RA, Gal G (1978) J Org Chem 43:1337

    Article  CAS  Google Scholar 

  37. cf Han G, McIntosh MC, Weinreb SM (1994) Tetrahedron Lett 35:5813 and references cited therein

    Article  CAS  Google Scholar 

  38. Ahman I, Somfai P (1992) Tetrahedron 48:9537

    Article  Google Scholar 

  39. Davis FA, Kluger EW (1976) J Am Chem Soc 98:302

    Article  CAS  Google Scholar 

  40. Prosyanik AV, Kol’tsov NY, Romanchenko VA, Belov VV, Burmistrov KS, Loban SV (1987) J Gen Chem USSR (Engl Trans) 23:335

    Google Scholar 

  41. For X-ray studies on the bis-N-tosyl imine of p-benzoquinone, see Shuets AE, Mishnev AF, Vleidelis YY (1978) Zh Strukt Khim 19:544

    Google Scholar 

  42. For 19F NMR studies and some chemistry of perfluorinated N-sulfonyl imines, see Petrov VA, Mlsna TE, Desmarteau DD (1994) J Fluorine Chem 68:277

    Article  CAS  Google Scholar 

  43. Ponzo VL, Kaufman TS (1995) Synlett 1149

    Google Scholar 

  44. Kaufman TS (1996) J Chem Soc Perkin Trans I 2997

    Google Scholar 

  45. Reuter M, German patent 847,006 (Chem Abstr (1956) 50:2669)

    Google Scholar 

  46. Nemoto H, Kubota Y, Yamamoto Y (1990) J Org Chem 55:4515 see also Lin Y-R, Zhou X-T, Dai L-X, Sun J (1997) J Org Chem 62:1799, Kai H, Iwamoto K, Chatani N, Murai S (1996) J Am Chem Soc 118:7634

    Article  CAS  Google Scholar 

  47. Shimada S, Saigo K, Abe M, Sudo A, Hasegawa M (1992) Chemistry Lett 1445

    Google Scholar 

  48. Weinreb SM, Sisko J, unpublished results

    Google Scholar 

  49. cf Krow GR, Pyun C, Marakowski J (1974) J Org Chem 39:2449

    Article  CAS  Google Scholar 

  50. Kobayashi S, Araki M, Ishitani H, Nagayama S, Hachiya I (1995) Synlett 233

    Google Scholar 

  51. Saigo K, Shimada S, Hasegawa M (1990) Chemistry Lett 905

    Google Scholar 

  52. Ralbovsky JL, Scola PM, Sugino E, Burgos-Garcis C, Weinreb SM, Parvez M (1996) Heterocycles 43:1497

    CAS  Google Scholar 

  53. Somfai P, Ahman J (1992) Tetrahedron Lett 33:3791

    CAS  Google Scholar 

  54. Lu Z-H, Zhou W-S (1993) J Chem Soc Perkin Trans I 393

    Google Scholar 

  55. Lu Z-H, Zhou W-S (1993) Tetrahedron 49:4659

    Article  CAS  Google Scholar 

  56. Zhou, W-S, Lu Z-H, Wang Z-M (1991) Tetrahedron Lett 32:1467

    Article  CAS  Google Scholar 

  57. Sisko J, Henry JR, Weinreb SM (1993) J Org Chem 58:4945

    Article  CAS  Google Scholar 

  58. cf Takano S, Iwabuchi Y, Ogasawara K (1987) J Am Chem Soc 109:5523

    Article  CAS  Google Scholar 

  59. Overman LE, Blumenkopf TA (1986) Chem Rev 86:857

    Article  Google Scholar 

  60. Fleming I, Dunogues J, Smithers R (1989) Org React 37:57

    CAS  Google Scholar 

  61. McIntosh MC, Weinreb SM (1993) J Org Chem 58:4823

    Article  CAS  Google Scholar 

  62. Garigipati RS, Tschaen DM, Weinreb SM (1990) J Am Chem Soc 112:3475. Weinreb SM (1995) in Studies in natural products chemistry (Rahman A, ed) Elsevier, Amsterdam, Vol 16 (Part J)p 3

    Article  CAS  Google Scholar 

  63. see also Magnus P, Lacour J, Coldham I, Mugrage B, Bauta WB (1995) Tetrahedron 51: 11087

    Article  CAS  Google Scholar 

  64. Volkmann RA (1991) Nucleophilic addition to imines and imine derivatives in Comprehensive organic synthesis (Trost BM, Fleming I, eds) Pergamon, Oxford, Vol 1, p. 355

    Google Scholar 

  65. Reetz MT, Jaeger R, Drewlies R, Hubel M (1991) Angew Chem Int Ed Engl 30:103 see also Hopman JCP, van den Berg E, Ollero Ollero L, Hiemstra H, Speckamp WN (1995) Tetrahedron Lett 36:4315

    Article  Google Scholar 

  66. Cherkauskas JP, Borzilleri RM, Sisko J, Weinreb SM (1995) Synlett 527

    Google Scholar 

  67. Cherkauskas JP, Klos AM, Borzilleri RM, Sisko J, Weinreb SM, Parvez M (1996) Tetrahedron 52:3135

    Article  CAS  Google Scholar 

  68. Zaugg HE (1965) Org React 14:52 see also Negash K, Nichols DE (1996) Tetrahedron Lett 37:6971. Ishizaki M, Hoshino O, Iitaka Y (1992) J Org Chem 57:7285

    CAS  Google Scholar 

  69. Il’in GF, Kolomiets AF, Sokol’skii GA (1979) J Org Chem USSR (Engl Trans) 15:2012

    Google Scholar 

  70. Hamley P, Holmes AB, Kee A, Ladduwahetty T, Smith DF (1991) Synlett 29

    Google Scholar 

  71. Monti L, Felici L (1940) Gazz Chim Ital 70:375

    CAS  Google Scholar 

  72. Weinreb SM (1991) Heterodienophile additions to dienes in Comprehensive organic synthesis (Trost BM, Fleming I, eds) Pergamon, Oxford, Vol 5, p 401

    Google Scholar 

  73. Kresze G, Albrecht R (1964) Chem Ber 97:490

    Article  CAS  Google Scholar 

  74. Kresze G, Wagner U (1972) Liebig’s Ann Chem 762:106

    Article  CAS  Google Scholar 

  75. Rijsenbrij PPM, Loven R, Wijnberg JBPA, Speckamp WN, Huisman HO (1972) Tetrahedron Lett 1425

    Google Scholar 

  76. Loven RP, Zunnebeld WA, Speckamp WN (1975) Tetrahedron 31:1723

    Article  CAS  Google Scholar 

  77. Kasper F, Dathe S (1985) J Prakt Chem 327:1041

    Article  CAS  Google Scholar 

  78. Krow G, Rodebaugh R, Marakowski J (1973) Tetrahedron Lett 1899

    Google Scholar 

  79. Krow GR, Dyun C, Rodebaugh R, Marakowski J (1974) Tetrahedron 30:2977

    Article  CAS  Google Scholar 

  80. see also Zunnebeld WA, Speckamp WN (1975) Tetrahedron 31:1717. In this example, poorer regioselectivity was observed

    Article  CAS  Google Scholar 

  81. Barco A, Benetti S, Baraldi PG, Moroder F, Pollini GP, Simoni D (1982) Liebig’s Ann Chem 960

    Google Scholar 

  82. Maggini M, Prato M, Scorrano G (1990) Tetrahedron Lett 31:6243

    Article  CAS  Google Scholar 

  83. Hohnes AB, Raithby PR, Thompson J, Baxter AJG, Dixon J (1983) J Chem Soc, Chem Commun 1491. Hohnes AB, Kee A, Ladduwahetty T, Smith DF (1990) J Chem Soc, Chem Commun 1412

    Google Scholar 

  84. Heintzelman GR, Weinreb SM, Parvez M (1996) J Org Chem 61:4594

    Article  CAS  Google Scholar 

  85. Hamada T, Sato H, Hikota M, Yonemitsu O (1989) Tetrahedron Lett 30:6405

    Article  CAS  Google Scholar 

  86. Hamada T, Zenkoh T, Sato H, Yonemitsu O (1991) ibid 32:1649

    Article  CAS  Google Scholar 

  87. Tripathy R, Franck RW, Onan KD (1988) J Am Chem Soc 110:3257

    Article  CAS  Google Scholar 

  88. Holmes AB, Thompson J, Baxter AJG, Dixon J (1985) J Chem Soc Chem Commun 37

    Google Scholar 

  89. Birkinshaw TN, Tabor AB, Holmes AB, Kaye P, Mayne PM (1988) J Chem Soc Chem Commun 1599

    Google Scholar 

  90. Birkinshaw TN, Tabor AB, Holmes AB, Raithby PR (1988) J Chem Soc Chem Commun 1602

    Google Scholar 

  91. Hamley P, Helmchen G, Holmes AB, Marshall DR, MacKinnon JWM, Smith DF, Ziller JW (1992) J Chem Soc Chem Commun 786

    Google Scholar 

  92. Poll T, Metter JO, Helmchen G (1985) Angew Chem Int Ed Engl 24:112

    Article  Google Scholar 

  93. McFarlane AK, Thomas G, Whiting A (1993) Tetrahedron Lett 34:2379

    Article  CAS  Google Scholar 

  94. McFarlane AK, Thomas G, Whiting A (1995) J Chem Soc Perkin Trans 1:2803

    Article  Google Scholar 

  95. Abramovitch RA, Stowers JR (1984) Heterocycles 22:671

    Article  CAS  Google Scholar 

  96. Abramovitch RA, Shinkai I, Mavunkel BJ, More KM, O’Connor S, Ooi GH, Pennington WT, Srinivasan PC, Stowers JR (1996) Tetrahedron 52:3339

    Article  CAS  Google Scholar 

  97. Fujii T, Kimura T, Furukawa N (1995) Tetrahedron Lett 36:1075

    Article  CAS  Google Scholar 

  98. Boger DL, Kasper AM (1989) J Am Chem Soc 111:1517

    Article  CAS  Google Scholar 

  99. Boger DL, Corbett WL, Wiggins JM (1990) J Org Chem 55:2999

    Article  CAS  Google Scholar 

  100. Boger DL, Curran TT (1990) J Org Chem 55:5439

    Article  CAS  Google Scholar 

  101. Boger DL, Corbett WL, Curran TT, Kasper AM (1991) J Am Chem Soc 113:1713

    Article  CAS  Google Scholar 

  102. see also Orsini F, Sala G (1989) Tetrahedron 45:6531

    Article  CAS  Google Scholar 

  103. Boger DL, Zhang M (1992) J Org Chem 57:3974

    Article  CAS  Google Scholar 

  104. Boger DL, Huter O, Mbiya K, Zhang M (1995) J Am Chem Soc 117:11839

    Article  CAS  Google Scholar 

  105. Novikova OP, Livantova LI, Zaitseva GS (1990) Zh Obsch Khim 59:2630

    Google Scholar 

  106. Zaitseva GS, Novikova OP, Livantsova LI, Petrosyan VS, Baukov YI (1992) Zh Obsch Khim 61:1389 see also Srirajan V, Deshmukh ARAS, Puranik VG, Bhawal BM (1996) Tetrahedron: Asymmetry 7:2733

    Google Scholar 

  107. For a review of imino ene reactions see: Borzilleri RM, Weinreb SM (1995) Synthesis 347

    Google Scholar 

  108. Achmatowicz O, Pietraszkiewicz M (1976) J Chem Soc Chem Commun 484

    Google Scholar 

  109. Achmatowicz O, Pietraszkiewicz M (1981) J Chem Soc Perkin Trans 1:2680

    Article  Google Scholar 

  110. Tschaen DM, Weinreb SM (1982) Tetrahedron Lett 23:3015

    Article  CAS  Google Scholar 

  111. Tschaen DM, Turos E, Weinreb SM (1984) J Org Chem 49:5058

    Article  CAS  Google Scholar 

  112. For a recent theoretical treatment of imino ene reactions, see Thomas BE, Houk KN (1993) J Am Chem Soc 115:790

    Article  CAS  Google Scholar 

  113. Braxmeier H, Kresze G (1985) Synthesis 683

    Google Scholar 

  114. Starflinger W, Kresze G, Huss K (1986) J Org Chem 51:37

    Article  CAS  Google Scholar 

  115. Mikami K, Kaneko M, Yajima T (1993) Tetrahedron Lett 34:4841

    Article  CAS  Google Scholar 

  116. Baumann H, Dulhaler RO (1988) Helv Chim Acta 71:1025

    Article  CAS  Google Scholar 

  117. Shimada T, Ando A, Takagi T, Koyama M, Miki T, Kumadaki I (1992) Chem Pharm Bull 40:1665

    CAS  Google Scholar 

  118. Davis FA, Weismiller MC, Lal GS, Chen BC, Przeslawski RM (1989) Tetrahedron Lett 30:1613

    Article  CAS  Google Scholar 

  119. Davis FA, Thimma Reddy R, Weismiller MC (1989) J Am Chem Soc 111:5964

    Article  CAS  Google Scholar 

  120. Chen BC, Murphy CK, Kumar A, Thimma Reddy R, Zhou P, Lewis BM, Gala D, Mergelsberg I, Scherer D, Buckley J, Dibenedetto D, Davis FA (1995) Org Synth 73:159

    Google Scholar 

  121. Towson JC, Weismiller MC, Lal GS, Sheppard AC, Davis FA, Org Synth 69:158

    Google Scholar 

  122. Davis FA, Thimma Reddy R, Han W, Reddy RE (1993) Pure Appl Chem 65:633

    Article  CAS  Google Scholar 

  123. Davis FA, Sheppard AC (1989) Tetrahedron 45:5703

    Article  CAS  Google Scholar 

  124. Glass RS, Hoy RC (1976) Tetrahedron Lett 1777 and 1781

    Google Scholar 

  125. Hayashi T, Kishi E, Soloshonok VA, Uozumi Y (1996) ibid 37:4969

    Article  CAS  Google Scholar 

  126. Li A-H, Dai L-X, Hou X-L (1996) J Chem Soc, Chem Commun 491

    Google Scholar 

  127. Li A-H, Dai L-X, Hou X-L (1996) J Chem Soc Perkin Trans I 867

    Google Scholar 

  128. Li A-H, Dai L-X Hou X-L, Chen M-B (1996) J Org Chem 61:4641

    Article  CAS  Google Scholar 

  129. Li A-H, Dai L-X, Hou X-L (1996) J Chem Soc Perkin Trans I 2725

    Google Scholar 

  130. Braun M, Opdenbusch K (1993) Angew Chem Int Ed Engl 32:578

    Article  Google Scholar 

  131. Ishitani H, Nagayama S, Kobayshi S (1996) J Org Chem 61:1902

    Article  CAS  Google Scholar 

  132. For new reactions of N-sulfonyl imines see Aggarwal VK, Thompson A, Jonez RVH, Standen MCH (1996) J Org Chem 61:8368

    Article  CAS  Google Scholar 

  133. For new reactions of N-sulfonyl imines Charette A, Giroux A (1996) Tetrahedron Lett 37:6669

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, The Pennsylvania State University, 16802, University Park, PA, USA

    Steven M. Weinreb

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  1. Steven M. Weinreb
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Peter Metz

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Weinreb, S.M. (1997). N-sulfonyl imines — Useful synthons in stereoselective organic synthesis. In: Metz, P. (eds) Stereoselective Heterocyclic Synthesis II. Topics in Current Chemistry, vol 190. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119248

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  • DOI: https://doi.org/10.1007/BFb0119248

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