Using a temporary silicon connection in stereoselective allylation with allylsilanes: application to the synthesis of stereodefined 1,2,4-triols

Julien Beignet; Liam Cox

Using a temporary silicon connection in stereoselective allylation with allylsilanes: application to the synthesis of stereodefined 1,2,4-triols

Julien Beignet, Liam Cox

Chemistry

Research output: Contribution to journal › Article

20 Citations (Scopus)

Abstract

Treatment of aldehyde 6 with TMSOTf, in the presence of a Bronsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.

Original language	English
Pages (from-to)	4231-4234
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	22
Publication status	Published - 1 Jan 2003

Cite this

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title = "Using a temporary silicon connection in stereoselective allylation with allylsilanes: application to the synthesis of stereodefined 1,2,4-triols",

abstract = "Treatment of aldehyde 6 with TMSOTf, in the presence of a Bronsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.",

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N2 - Treatment of aldehyde 6 with TMSOTf, in the presence of a Bronsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.

AB - Treatment of aldehyde 6 with TMSOTf, in the presence of a Bronsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.

UR - https://www.scopus.com/pages/publications/0344514091

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SP - 4231

EP - 4234

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Using a temporary silicon connection in stereoselective allylation with allylsilanes: application to the synthesis of stereodefined 1,2,4-triols

Abstract

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