Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 11-12, Pages 1885-1890Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.200800251
Keywords
lactones; N-heterocyclic carbenes; organocatalysis; stereoselectivity; umpolung
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Funding
- Chinese Academy of Sciences
- National Natural Science Foundation of China
- Sciencc and Technology Commission of Shanghai Municipality [07pj14106, 07JC104063]
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4,5,5-Trisubstituted gamma-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).
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