Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

Masatoshi Shibuya; Shinichiro Ito; Michiyasu Takahashi; Yoshiharu Iwabuchi

doi:10.1021/ol048210u

Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

Masatoshi Shibuya, Shinichiro Ito, Michiyasu Takahashi, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

66 Citations (Scopus)

Abstract

(Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

Original language	English
Pages (from-to)	4303-4306
Number of pages	4
Journal	Organic letters
Volume	6
Issue number	23
DOIs	https://doi.org/10.1021/ol048210u
Publication status	Published - 2004 Nov 11

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO",

abstract = "(Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.",

author = "Masatoshi Shibuya and Shinichiro Ito and Michiyasu Takahashi and Yoshiharu Iwabuchi",

year = "2004",

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AU - Shibuya, Masatoshi

AU - Ito, Shinichiro

AU - Takahashi, Michiyasu

AU - Iwabuchi, Yoshiharu

PY - 2004/11/11

Y1 - 2004/11/11

N2 - (Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

AB - (Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

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