Display options
Cite
Chiarucci M, Locritani M, Cera G, et al. Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols. Beilstein J Org Chem. 2011;7:1198-204doi: 10.3762/bjoc.7.139.
Chiarucci, M., Locritani, M., Cera, G., & Bandini, M. (2011). Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols. Beilstein journal of organic chemistry, 71198-204. https://doi.org/10.3762/bjoc.7.139
Chiarucci, Michel, et al. "Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols." Beilstein journal of organic chemistry vol. 7 (2011): 1198-204. doi: https://doi.org/10.3762/bjoc.7.139
Chiarucci M, Locritani M, Cera G, Bandini M. Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols. Beilstein J Org Chem. 2011;7:1198-204. doi: 10.3762/bjoc.7.139. Epub 2011 Sep 01. PMID: 21977203; PMCID: PMC3182428.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2011;7:1198-204. doi: 10.3762/bjoc.7.139. Epub 2011 Sep 01.

Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols.

Beilstein journal of organic chemistry

Michel Chiarucci, Mirko Locritani, Gianpiero Cera, Marco Bandini

Affiliations

  1. Dipartimento di Chimica "G. Ciamician", Alma Mater Studiorum - Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.

PMID: 21977203 PMCID: PMC3182428 DOI: 10.3762/bjoc.7.139

Abstract

Gold(I)-N-heterocyclic carbene (NHC) complexes proved to be a reliable catalytic system for the direct synthesis of functionalized γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with primary alcohols. Good isolated chemical yields were obtained for a range of malonyl and acetate derivatives. The good performance in reagent-grade solvents and the functional group/moisture tolerance make this catalytic process a promising route for the synthesis of architecturally complex polycyclic structures.

Keywords: alcohol; butyrolactone; carbene; gold-catalysis; intramolecular oxaallylic alkylation

References

  1. J Am Chem Soc. 2008 Dec 31;130(52):17642-3 - PubMed
  2. Angew Chem Int Ed Engl. 2007;46(32):6184-7 - PubMed
  3. Angew Chem Int Ed Engl. 2007;46(22):4042-59 - PubMed
  4. Chem Asian J. 2009 Aug 3;4(8):1230-6 - PubMed
  5. J Am Chem Soc. 2005 Oct 19;127(41):14180-1 - PubMed
  6. Chem Rev. 2008 Aug;108(8):3351-78 - PubMed
  7. Org Lett. 2009 Jan 1;11(1):121-4 - PubMed
  8. Angew Chem Int Ed Engl. 2011 Feb 1;50(5):994-5 - PubMed
  9. J Org Chem. 2008 Aug 1;73(15):5795-805 - PubMed
  10. Chem Soc Rev. 2009 Aug;38(8):2269-81 - PubMed
  11. Chem Rev. 2007 Jul;107(7):3180-211 - PubMed
  12. Org Biomol Chem. 2008 Jul 7;6(13):2426-33 - PubMed
  13. J Am Chem Soc. 2004 Jun 9;126(22):6884-5 - PubMed
  14. Chem Commun (Camb). 2010 Jan 28;46(4):577-9 - PubMed
  15. Angew Chem Int Ed Engl. 2007;46(19):3410-49 - PubMed
  16. Org Lett. 2003 Mar 6;5(5):621-4 - PubMed
  17. Org Biomol Chem. 2009 Apr 21;7(8):1501-7 - PubMed
  18. Org Lett. 2011 Mar 18;13(6):1334-7 - PubMed
  19. Chem Commun (Camb). 2010 Sep 28;46(36):6849-51 - PubMed
  20. Chem Rev. 2008 Aug;108(8):3239-65 - PubMed
  21. Chemistry. 2010 Oct 4;16(37):11271-4 - PubMed
  22. Org Lett. 2010 Mar 19;12(6):1184-7 - PubMed
  23. Angew Chem Int Ed Engl. 2010 Jul 19;49(31):5232-41 - PubMed
  24. Chem Rev. 2008 Aug;108(8):3326-50 - PubMed
  25. Angew Chem Int Ed Engl. 2009;48(47):8948-51 - PubMed
  26. Bioorg Med Chem. 2010 Apr 1;18(7):2549-58 - PubMed
  27. Acc Chem Res. 2011 Feb 15;44(2):91-100 - PubMed
  28. Nature. 2007 Mar 22;446(7134):395-403 - PubMed
  29. Angew Chem Int Ed Engl. 2007;46(17):3139-43 - PubMed
  30. Org Lett. 2011 Mar 18;13(6):1330-3 - PubMed
  31. Org Biomol Chem. 2010 Jul 21;8(14):3207-10 - PubMed
  32. Angew Chem Int Ed Engl. 2009;48(50):9533-7 - PubMed
  33. Chemistry. 2010 Dec 27;16(48):14272-7 - PubMed
  34. Org Lett. 2008 Feb 21;10(4):669-71 - PubMed
  35. Nat Prod Rep. 2005 Dec;22(6):696-716 - PubMed
  36. Chem Soc Rev. 2008 Sep;37(9):1776-82 - PubMed
  37. Angew Chem Int Ed Engl. 2011 May 9;50(20):4649-53 - PubMed

Publication Types