期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 30, 页码 9132-9139出版社
WILEY-BLACKWELL
DOI: 10.1002/chem.201000840
关键词
anti-aldol; catalysis; enolates; ketenes; pyridinium
资金
- TH [TH-30/04-2]
- Swiss National Science Foundation (SNF)
- F. Hoffmann-La Roche
The development of the first trans-selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4-disubstituted beta-lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could also be applied to aromatic aldehydes and offers broad applicability (29 examples). The utility was further demonstrated by nucleophilic ring-opening reactions that provide highly enantiomerically enriched anti-aldol products.
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