Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid

A. Krief; W. Dumont; A. Kremer

doi:10.1016/j.tetlet.2009.03.001

Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid

A. Krief, W. Dumont, A. Kremer

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

Abstract

cis-Chrysanthemic acid has been prepared in a few steps from dimethyldimedone via dibromination at alpha positions of each carbonyl carbons. The trans-dibromide which is almost exclusively formed has been isomerized to its cis-stereoisomer by highly chemoselective tandem H/K-K/H exchanges involving potassium bases at low temperature (

Original language	English
Pages (from-to)	2398-2401
Journal	Tetrahedron Letters
Volume	50
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.001
Publication status	Published - 20 May 2009

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10.1016/j.tetlet.2009.03.001

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title = "Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid",

abstract = "cis-Chrysanthemic acid has been prepared in a few steps from dimethyldimedone via dibromination at alpha positions of each carbonyl carbons. The trans-dibromide which is almost exclusively formed has been isomerized to its cis-stereoisomer by highly chemoselective tandem H/K-K/H exchanges involving potassium bases at low temperature (",

author = "A. Krief and W. Dumont and A. Kremer",

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Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid. / Krief, A.; Dumont, W.; Kremer, A.
In: Tetrahedron Letters, Vol. 50, No. 20, 20.05.2009, p. 2398-2401.

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

TY - JOUR

T1 - Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid

AU - Krief, A.

AU - Dumont, W.

AU - Kremer, A.

PY - 2009/5/20

Y1 - 2009/5/20

N2 - cis-Chrysanthemic acid has been prepared in a few steps from dimethyldimedone via dibromination at alpha positions of each carbonyl carbons. The trans-dibromide which is almost exclusively formed has been isomerized to its cis-stereoisomer by highly chemoselective tandem H/K-K/H exchanges involving potassium bases at low temperature (

AB - cis-Chrysanthemic acid has been prepared in a few steps from dimethyldimedone via dibromination at alpha positions of each carbonyl carbons. The trans-dibromide which is almost exclusively formed has been isomerized to its cis-stereoisomer by highly chemoselective tandem H/K-K/H exchanges involving potassium bases at low temperature (

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DO - 10.1016/j.tetlet.2009.03.001

M3 - Article

AN - SCOPUS:63349100263

SN - 0040-4039

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SP - 2398

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JO - Tetrahedron Letters

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Novel synthesis of (d,l)-cis-chrysanthemic acid involving α,α′-dibromination of 2,2,5,5-tetramethylcyclohexane-1,3-dione: Application to the enantioselective synthesis of (1R)-cis-chrysanthemic acid

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