N-triflylthiophosphoramide catalyzed enantioselective mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones

Cheol Hong Cheon; Hisashi Yamamoto

doi:10.1021/ol100233t

N-triflylthiophosphoramide catalyzed enantioselective mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones

Cheol Hong Cheon, Hisashi Yamamoto

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

Abstract

The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature.

Original language	English
Pages (from-to)	2476-2479
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	11
DOIs	https://doi.org/10.1021/ol100233t
Publication status	Published - 2010 Jun 4
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol100233t

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abstract = "The first Br{\o}nsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Br{\o}nsted acid to the Br{\o}nsted acid itself depending on the reaction temperature.",

author = "Cheon, {Cheol Hong} and Hisashi Yamamoto",

year = "2010",

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doi = "10.1021/ol100233t",

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Y1 - 2010/6/4

N2 - The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature.

AB - The first Brønsted acid catalyzed asymmetric Mukaiyama aldol reaction of aldehydes using silyl enol ethers of ketones as nucleophiles has been reported. A variety of aldehydes and silyl enol ethers of ketones afforded the aldol products in excellent yields and good to excellent enantioselectivities. Mechanistic studies revealed that the actual catalyst may be changed from the silylated Brønsted acid to the Brønsted acid itself depending on the reaction temperature.

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N-triflylthiophosphoramide catalyzed enantioselective mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones

Abstract

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