Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes

Wei Wang; Hao Li; Jian Wang

doi:10.1021/ol0503337

Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes

Wei Wang, Hao Li, Jian Wang

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87 Scopus citations

Abstract

(Chemical Equation Presented) A highly enantioselective, organocatalytic Mukaiyama-Michael addition reaction of silyl ethers and α,β- unsaturated aldehydes has been developed. The process, catalyzed by MacMillan's chiral imidazolidinone, affords δ-keto aldehydes in high yields (56-87%) and high enantioselectivities (85-97% ee). Moreover, the reaction is applicable to a wide range of silyl ethers and α,β-unsaturated aldehydes and, as such, provides access to a range of important synthetic building blocks.

Original language	English (US)
Pages (from-to)	1637-1639
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	8
DOIs	https://doi.org/10.1021/ol0503337
State	Published - Apr 14 2005
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0503337

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title = "Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes",

abstract = "(Chemical Equation Presented) A highly enantioselective, organocatalytic Mukaiyama-Michael addition reaction of silyl ethers and α,β- unsaturated aldehydes has been developed. The process, catalyzed by MacMillan's chiral imidazolidinone, affords δ-keto aldehydes in high yields (56-87%) and high enantioselectivities (85-97% ee). Moreover, the reaction is applicable to a wide range of silyl ethers and α,β-unsaturated aldehydes and, as such, provides access to a range of important synthetic building blocks.",

author = "Wei Wang and Hao Li and Jian Wang",

year = "2005",

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doi = "10.1021/ol0503337",

language = "English (US)",

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journal = "Organic Letters",

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T1 - Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes

AU - Wang, Wei

AU - Li, Hao

AU - Wang, Jian

PY - 2005/4/14

Y1 - 2005/4/14

N2 - (Chemical Equation Presented) A highly enantioselective, organocatalytic Mukaiyama-Michael addition reaction of silyl ethers and α,β- unsaturated aldehydes has been developed. The process, catalyzed by MacMillan's chiral imidazolidinone, affords δ-keto aldehydes in high yields (56-87%) and high enantioselectivities (85-97% ee). Moreover, the reaction is applicable to a wide range of silyl ethers and α,β-unsaturated aldehydes and, as such, provides access to a range of important synthetic building blocks.

AB - (Chemical Equation Presented) A highly enantioselective, organocatalytic Mukaiyama-Michael addition reaction of silyl ethers and α,β- unsaturated aldehydes has been developed. The process, catalyzed by MacMillan's chiral imidazolidinone, affords δ-keto aldehydes in high yields (56-87%) and high enantioselectivities (85-97% ee). Moreover, the reaction is applicable to a wide range of silyl ethers and α,β-unsaturated aldehydes and, as such, provides access to a range of important synthetic building blocks.

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JO - Organic Letters

JF - Organic Letters

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ER -

Enantioselective organocatalytic Mukaiyama-Michael addition of silyl enol ethers to α,β-unsaturated aldehydes

Abstract

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