Diastereoselective aldol addition reactions of a chiral methyl ketone trichlorosilyl enolate under lewis base catalysis

S. E. Denmark; S. Fujimori

doi:10.1055/s-2001-14652

Diastereoselective aldol addition reactions of a chiral methyl ketone trichlorosilyl enolate under lewis base catalysis

S. E. Denmark, S. Fujimori

Chemistry

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

Abstract

The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.

Original language	English (US)
Pages (from-to)	1024-1029
Number of pages	6
Journal	Synlett
Issue number	SPEC. ISS
DOIs	https://doi.org/10.1055/s-2001-14652
State	Published - 2001

Keywords

Aldol addition
Diastereoselection
Lewis base catalysis
Trichlorosilyl enolate

ASJC Scopus subject areas

Organic Chemistry

Online availability

10.1055/s-2001-14652

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title = "Diastereoselective aldol addition reactions of a chiral methyl ketone trichlorosilyl enolate under lewis base catalysis",

abstract = "The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.",

keywords = "Aldol addition, Diastereoselection, Lewis base catalysis, Trichlorosilyl enolate",

author = "Denmark, {S. E.} and S. Fujimori",

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AU - Denmark, S. E.

AU - Fujimori, S.

PY - 2001

Y1 - 2001

N2 - The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.

AB - The trichlorosilyl enolate of a chiral methyl ketone bearing an oxygen substituent (OTBS) on the β-position undergoes highly diastereoselective aldol addition to a variety of achiral aldehydes in good yield. The stereochemical course of the reaction is primarily controlled by the configuration of the chiral phosphoramide which serves as an effective catalyst for this transformation.

KW - Aldol addition

KW - Diastereoselection

KW - Lewis base catalysis

KW - Trichlorosilyl enolate

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ER -

Diastereoselective aldol addition reactions of a chiral methyl ketone trichlorosilyl enolate under lewis base catalysis

Abstract

Keywords

ASJC Scopus subject areas

Online availability

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