Skip to main content
SpringerLink
Log in

Synthesis of Lactams by Metathesis Reactions

  • Chapter
  • First Online:
Synthesis of Heterocycles by Metathesis Reactions

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 47))

Abstract

The use of metathesis for the synthesis of lactams has become very important in the last decade. This reaction allows the synthesis of very diverse lactam-containing compounds: from simple building blocks to refined macrolactams or polycyclic systems. The arsenal of metathesis reactions ranges from ring-closing metathesis (RCM) to ring-rearrangement metathesis (RRM) to ring-closing enyne metathesis (RCEYM) or cross metathesis (CM). The strategic deployment of such reactions for the synthesis of lactams will be described in this chapter, with a discussion on factors that govern the metathesis reaction.

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 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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

Similar content being viewed by others

References

  1. Nubbemeyer U (2001) Top Curr Chem 216:125–196

    Article  CAS  Google Scholar 

  2. Pace V, Holzer W (2013) Austr J Chem 66:507–512

    CAS  Google Scholar 

  3. Hassan HMA (2010) Chem Commun 46:9100–9106

    Article  CAS  Google Scholar 

  4. Fustero S, Mateu N, Albert L, Acena JL (2009) J Org Chem 74:4429–4432

    Article  CAS  Google Scholar 

  5. Ku IW, Kang SB, Keum G, Kim Y (2011) Bull Korean Chem Soc 32:3167–3170

    Article  CAS  Google Scholar 

  6. Khadem S, Udachin KA, Arya P (2010) Synlett 199–202

    Google Scholar 

  7. Spiess S, Berthold C, Weihofen R, Helmchen G (2007) Org Biomol Chem 5:2357–2360

    Article  CAS  Google Scholar 

  8. Krishna PR, Reddy BK (2013) Helv Chim Acta 96:1564–1569

    Article  Google Scholar 

  9. Shi YC, Wang SG, Yin Q, You SL (2014) Org Chem Front 1:39–43

    Article  CAS  Google Scholar 

  10. Fiorelli C, Savoia D (2007) J Org Chem 72:6022–6028

    Article  CAS  Google Scholar 

  11. Sirvent JA, Foubelo F, Yus M (2014) J Org Chem 79:1356–1367

    Article  CAS  Google Scholar 

  12. Park SH, Kang HJ, Ko S, Park S, Chang S (2001) Tetrahedron Asymm 12:2621–2624

    Article  CAS  Google Scholar 

  13. Yadav JS, Jayasudhan Reddy Y, Addi Narayana Reddy P, Subba Reddy BV (2013) Org Lett 15:546–549

    Article  CAS  Google Scholar 

  14. Subba Reddy BV, Ghanty S, Siva Senkar Reddy N, Jayasudhan Reddy Y, Yadav JS (2014) Synth Commun 44:1658–1663

    Article  CAS  Google Scholar 

  15. Pritchard DR, Wilden JD (2010) Tetrahedron Lett 51:1819–1821

    Article  CAS  Google Scholar 

  16. Laventine DL, Cullis PM, Garcia MD, Jenkins PR (2009) Tetrahedron Lett 50:3657–3660

    Article  CAS  Google Scholar 

  17. Reddy PT, Quevillon S, Gan Z, Forbes N, Leek DM, Arya P (2006) J Comb Chem 8:856–871

    Article  CAS  Google Scholar 

  18. Lebrun S, Couture A, Deniau E, Grandclaudon P (2011) Synthesis 669–673

    Google Scholar 

  19. Arya P, Couve-Bonnaire S, Durieux P, Laforce D, Kumar R, Leek DM (2004) J Comb Chem 6:735–745

    Article  CAS  Google Scholar 

  20. Toumi M, Couty F, Evano G (2008) J Org Chem 73:1270–1281

    Article  CAS  Google Scholar 

  21. Kim HM, Lee K, Park BW, Ryu DK, Kim K, Lee CW, Park SK, Han JW, Lee HY, Lee HY, Han G (2006) Bioorg Med Chem Lett 16:4068–4070

    Article  CAS  Google Scholar 

  22. Manzoni L, Colombo M, Scolastico C (2004) Tetrahedron Lett 45:2623–2625

    Article  CAS  Google Scholar 

  23. Chen Y, Zhang H, Nan F (2004) J Com Chem 6:684–687

    Article  CAS  Google Scholar 

  24. Marhold M, Buer A, Hiemstra H, van Maarseveen JH, Haufe G (2004) Tetrahedron Lett 45:57–60

    Article  CAS  Google Scholar 

  25. Toueg J, Prunet J (2006) Synlett 2807–2811

    Google Scholar 

  26. Leonetti F, Muncipinto G, Stefanachi A, Nicolotti O, Cellamare S, Catto M, Pisanai L, Pellegrino G, Carotti A (2012) Tetrahedron Lett 53:4114–4116

    Article  CAS  Google Scholar 

  27. Donohoe TJ, Fishlock LP, Procopiou PA (2008) Synthesis 2665–2667

    Google Scholar 

  28. Lebrun S, Couture A, Deniau E, Grandclaudon P (2008) Synthesis 2771–2776

    Google Scholar 

  29. Spino C, Boisvert L, Douville J, Roy S, Lauzon S, Minville J, Gagnon D, Beaumier F, Chabot C (2006) J Organomet Chem 691:5336–5355

    Article  CAS  Google Scholar 

  30. Bensa D, Coldham I, Feinaugle P, Pathak RB, Butlin RJ (2008) Org Biomol Chem 6:1410–1415

    Article  CAS  Google Scholar 

  31. Daly M, Gill K, Sime M, Simpson GL, Sutherland A (2011) Org Biomol Chem 9:6761–6770

    Article  CAS  Google Scholar 

  32. Kamimura A, Tanaka K, Hayashi T, Omata Y (2006) Tetrahedron Lett 47:3625–3627

    Article  CAS  Google Scholar 

  33. Hassan HMA, Brown FK (2010) Chem Commun 46:3013–3015

    Article  CAS  Google Scholar 

  34. Fuhshuku K, Asano Y (2012) Tetrahedron 68:6651–6655

    Article  CAS  Google Scholar 

  35. Del Valle JR, Goodman M (2004) J Org Chem 69:8946–8948

    Article  Google Scholar 

  36. Jäkel M, Qu J, Schnitzer T, Helmchen G (2013) Chem Eur J 19:16746–16755

    Article  Google Scholar 

  37. Watson KD, Carosso S, Miller MJ (2013) Org Lett 15:358–361

    Article  CAS  Google Scholar 

  38. Guérin D, Gaumont AC, Dez I, Mauduit M, Couve-Bonnaire S, Pannecoucke X (2014) ACS Catal 4:2374–2378

    Article  Google Scholar 

  39. Schurgers B, Brigou B, Urbanczyk-Lipkowska Z, Tourwé D, Ballet S, De Proft F, Van Lommen G, Verniest G (2014) Org Lett 16:3712–3715

    Article  CAS  Google Scholar 

  40. Satyanarayana G, Helmchen G (2014) Eur J Org Chem 2242–2252

    Google Scholar 

  41. Creighton CJ, Leo GC, Du Y, Reitz AB (2004) Bioorg Med Chem 12:4375–4385

    Article  CAS  Google Scholar 

  42. Williams RM, Liu J (1998) J Org Chem 63:2130–2132

    Article  CAS  Google Scholar 

  43. Duggan HME, Hitchcock PB, Young DW (2005) Org Biomol Chem 3:2287–2295

    Article  CAS  Google Scholar 

  44. Brady RM, Khakham Y, Lessene G, Baell JB (2011) Org Biomol Chem 9:656–658

    Article  CAS  Google Scholar 

  45. Bieraugel H, Jansen TP, Schoemaker HE, Hiemstra H, van Maarseveen JH (2002) Org Lett 4:2673–2674

    Article  Google Scholar 

  46. Dutton BL, Kitson RRA, Parry-Morris S, Roe SM, Prodromou C, Moody CJ (2014) Org Biomol Chem 12:1328–1340

    Article  CAS  Google Scholar 

  47. Szostak M, Aubé J (2009) Org Lett 11:3878–3881

    Article  CAS  Google Scholar 

  48. Pal APJ, Kadigachalam P, Mallick A, Doddi VR, Vankar YD (2011) Org Biomol Chem 9:809–819

    Article  CAS  Google Scholar 

  49. Fustero S, Baez C, Sanchez-Rosello M, Asensio A, Miro J, del Pozo C (2012) Synthesis 44:1863–1873

    Article  CAS  Google Scholar 

  50. Yang Q, Lai YY, Xiao WJ, Alper H (2008) Tetrahedron Lett 49:7334–7336

    Article  CAS  Google Scholar 

  51. Arimitsu S, Hammond GB (2010) Beilstein J Org Chem 6:48

    Article  Google Scholar 

  52. Huang J, Xiong H, Hsung RP, Rameshkumar C, Mulder JA, Grebe TP (2002) Org Lett 4:2417–2420

    Article  CAS  Google Scholar 

  53. Wroleski A, Sahasrabudhe K, Aubé J (2002) J Am Chem Soc 124:9974–9975

    Article  Google Scholar 

  54. Aljarilla A, Plumet J (2008) Eur J Org Chem 3984–3990

    Google Scholar 

  55. Buchert M, Meinke S, Prenzel AHGP, Deppermann N, Maison W (2006) Org Lett 8:5553–5556

    Article  Google Scholar 

  56. Calvet G, Blanchard N, Kouklovsky C (2007) Org Lett 9:1485–1488

    Article  CAS  Google Scholar 

  57. Vincent G, Kouklovsky C (2011) Chem Eur J 17:2972–2980

    Article  CAS  Google Scholar 

  58. Vincent G, Guillot R, Kouklovsky C (2011) Angew Chem Int Ed 50:1350–1353

    Article  CAS  Google Scholar 

  59. Nadany AE, Mckendrick JE (2007) Synlett 1663–1666

    Google Scholar 

  60. Maechling S, Norman SE, McKendrick JE, Basra S, Koppner K, Blechert S (2006) Tetrahedron Lett 47:189–192

    Article  CAS  Google Scholar 

  61. Spandl RJ, Rudyk H, Spring DR (2008) Chem Commun 3001–3003

    Google Scholar 

  62. Sello JK, Andreana PR, Lee D, Schreiber SL (2003) Org Lett 5:4125–4127

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Université Paris-Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques (MS&MT), Bat. 410, 15 rue Georges Clemenceau, 91405, Orsay, France

    Guillaume Vincent

Authors
  1. Guillaume Vincent
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guillaume Vincent .

Editor information

Editors and Affiliations

  1. School of Chemistry, University of Glasgow, Glasgow, United Kingdom

    Joëlle Prunet

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Vincent, G. (2015). Synthesis of Lactams by Metathesis Reactions. In: Prunet, J. (eds) Synthesis of Heterocycles by Metathesis Reactions. Topics in Heterocyclic Chemistry, vol 47. Springer, Cham. https://doi.org/10.1007/7081_2015_144

Download citation

Publish with us

Policies and ethics

Search

Navigation