A highly enantioselective one-pot synthesis of homoallylic alcohols via tandem asymmetric allyl transfer/olefin cross metathesis

Cheng Hsia Angeline Lee; Teck Peng Loh

doi:10.1016/j.tetlet.2005.11.078

A highly enantioselective one-pot synthesis of homoallylic alcohols via tandem asymmetric allyl transfer/olefin cross metathesis

Cheng Hsia Angeline Lee, Teck Peng Loh^*

^*Corresponding author for this work

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

20 Citations (Scopus)

Abstract

A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demonstrated in a short synthesis of a low boiling point intermediate for grahamimycin A.

Original language	English
Pages (from-to)	809-812
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2005.11.078
Publication status	Published - Jan 30 2006
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Allyl transfer
Homoallylic alcohols
Olefin cross metathesis
Tandem reactions

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10.1016/j.tetlet.2005.11.078

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N2 - A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demonstrated in a short synthesis of a low boiling point intermediate for grahamimycin A.

AB - A highly enantioselective one-pot synthesis of linear homoallylic alcohols with terminal ester functionality has been achieved. The reactions were controlled by ordered addition of reagents and catalysts, ensuring complete consumption of aldehyde. The synthetic utility of this strategy has been demonstrated in a short synthesis of a low boiling point intermediate for grahamimycin A.

KW - Allyl transfer

KW - Homoallylic alcohols

KW - Olefin cross metathesis

KW - Tandem reactions

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ER -

A highly enantioselective one-pot synthesis of homoallylic alcohols via tandem asymmetric allyl transfer/olefin cross metathesis

Abstract

ASJC Scopus Subject Areas

Keywords

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