Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

Mark McLaughlin; Matthew J. Cook

doi:10.1021/jo202560g

Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

Mark McLaughlin
, Matthew J. Cook

School of Chemistry and Chemical Engineering

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

26 Citations (Scopus)

Abstract

A one-pot isomerization–Claisen protocol has been developed for the synthesis of highly substituted allylsilanes. Monosilylated divinyl ethers can be isomerized using a cationic iridium(I) catalyst followed by a thermal Claisen rearrangement to provide the allylsilanes in excellent yields and diastereoselectivities.

Original language	English
Pages (from-to)	2058-2063
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	77
Issue number	4
Early online date	10 Jan 2012
DOIs	https://doi.org/10.1021/jo202560g
Publication status	Published - 17 Feb 2012

ASJC Scopus subject areas

Organic Chemistry

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title = "Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes",

abstract = "A one-pot isomerization–Claisen protocol has been developed for the synthesis of highly substituted allylsilanes. Monosilylated divinyl ethers can be isomerized using a cationic iridium(I) catalyst followed by a thermal Claisen rearrangement to provide the allylsilanes in excellent yields and diastereoselectivities.",

author = "Mark McLaughlin and Cook, \{Matthew J.\}",

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journal = "Journal of Organic Chemistry",

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T1 - Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

AU - McLaughlin, Mark

AU - Cook, Matthew J.

PY - 2012/2/17

Y1 - 2012/2/17

N2 - A one-pot isomerization–Claisen protocol has been developed for the synthesis of highly substituted allylsilanes. Monosilylated divinyl ethers can be isomerized using a cationic iridium(I) catalyst followed by a thermal Claisen rearrangement to provide the allylsilanes in excellent yields and diastereoselectivities.

AB - A one-pot isomerization–Claisen protocol has been developed for the synthesis of highly substituted allylsilanes. Monosilylated divinyl ethers can be isomerized using a cationic iridium(I) catalyst followed by a thermal Claisen rearrangement to provide the allylsilanes in excellent yields and diastereoselectivities.

U2 - 10.1021/jo202560g

DO - 10.1021/jo202560g

M3 - Article

SN - 0022-3263

VL - 77

SP - 2058

EP - 2063

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Domino Alkene-Isomerization–Claisen Rearrangement Strategy to Substituted Allylsilanes

Abstract

ASJC Scopus subject areas

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