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- Ibrahem, Ismail, et al.
(författare)
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Enantioselective Conjugate Silyl Additions to alpha,beta-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts
- 2011
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Ingår i: Advanced Synthesis and Catalysis. - : Wiley. - 1615-4150 .- 1615-4169. ; 353:2-3, s. 245-252
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Tidskriftsartikel (refereegranskat)abstract
- 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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