Base-Base Bifunctional Catalysis: A Practical Strategy for Asymmetric Michael Addition of Malonates to α,β-Unsaturated Aldehydes

Lewis base–Brønsted base bifunctional catalysis is a novel and practical strategy for the asymmetric Michael addition. The addition of malonates to a series of α,β‐unsaturated aldehydes can take place under base–base bifunctional catalytic conditions using 0.5–5 mol% of (S)‐2‐[diphenyl(trimethylsily...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2008-06, Vol.350 (9), p.1383-1389
Main Authors: Wang, Yongcan, Li, Pengfei, Liang, Xinmiao, Ye, Jinxing
Format: Article
Language:English
Subjects:
aldehydes
asymmetric catalysis
bifunctional catalysis
malonates
Michael addition
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Summary:Lewis base–Brønsted base bifunctional catalysis is a novel and practical strategy for the asymmetric Michael addition. The addition of malonates to a series of α,β‐unsaturated aldehydes can take place under base–base bifunctional catalytic conditions using 0.5–5 mol% of (S)‐2‐[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as catalyst and 5–30 mol% of lithium 4‐fluorobenzoate as additive base with up to 99% ee.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800070