期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 353, 期 2-3, 页码 245-252出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000908
关键词
asymmetric catalysis; organocatalysis; beta-silyl aldehydes; transition metal catalysis; alpha,beta-unsaturated aldehydes
资金
- Mid Sweden University
- Swedish National Research Council (V.R.)
- Wenner-Gren Foundations
- VR
We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to alpha,beta-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding beta-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction can also generate a quaternary stereocenter with good enantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.
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