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

@article{285cb51107ac49ae840f4146d7b72a81,

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.",

author = "Julien Beignet and Liam Cox",

year = "2003",

month = jan,

day = "1",

language = "English",

volume = "5",

pages = "4231--4234",

journal = "Organic Letters",

publisher = "American Chemical Society",

number = "22",

}

TY - JOUR

T1 - Using a temporary silicon connection in stereoselective allylation with allylsilanes: application to the synthesis of stereodefined 1,2,4-triols

AU - Beignet, Julien

AU - Cox, Liam

PY - 2003/1/1

Y1 - 2003/1/1

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.

M3 - Article

VL - 5

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

Fingerprint

Cite this