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

Cheol-Hong Cheon, Hisashi Yamamoto

Research output: Contribution to journalArticle

59 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 languageEnglish
Pages (from-to)2476-2479
Number of pages4
JournalOrganic Letters
Volume12
Issue number11
DOIs
Publication statusPublished - 2010 Jun 4
Externally publishedYes

Fingerprint

Ethers
Ketones
aldehydes
Aldehydes
ketones
ethers
acids
Acids
Nucleophiles
Enantioselectivity
nucleophiles
catalysts
Catalysts
Temperature
products
3-hydroxybutanal
temperature

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

N-triflylthiophosphoramide catalyzed enantioselective mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones. / Cheon, Cheol-Hong; Yamamoto, Hisashi.

In: Organic Letters, Vol. 12, No. 11, 04.06.2010, p. 2476-2479.

Research output: Contribution to journalArticle

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