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Full Paper
Stereoselective Synthesis of γ-Butyrolactones via Organocatalytic Annulations of Enals and Keto Esters
Article first published online: 24 JUL 2008
DOI: 10.1002/adsc.200800251
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Li, Y., Zhao, Z.-A., He, H. and You, S.-L. (2008), Stereoselective Synthesis of γ-Butyrolactones via Organocatalytic Annulations of Enals and Keto Esters. Adv. Synth. Catal., 350: 1885–1890. doi: 10.1002/adsc.200800251
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 24 JUL 2008
- Manuscript Revised: 16 JUN 2008
- Manuscript Received: 26 APR 2008
Funded by
- Chinese Academy of Sciences
- National Natural Science Foundation of China
- Science and Technology Commission of Shanghai Municipality. Grant Number: 07pj14106, 07 JC14063
Keywords:
- lactones;
- N-heterocyclic carbenes;
- organocatalysis;
- stereoselectivity;
- umpolung
Abstract
4,5,5-Trisubstituted γ-butyrolactones bearing two stereocenters including one quaternary carbon center have been synthesized in excellent yields via N-heterocyclic carbene-catalyzed annulations of enals and ketoesters. Chiral N-heterocyclic carbenes were used to tune the diastereoselectivity up to an 83/17 cis/trans ratio and the enantioselectivity up to 78% ee (trans isomer).