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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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 languageEnglish
Pages (from-to)2398-2401
JournalTetrahedron Letters
Volume50
Issue number20
DOIs
Publication statusPublished - 20 May 2009

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NSC 153174
Stereoisomerism
Potassium
Carbon
Temperature
chrysanthemic acid

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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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AU - Krief, A.

AU - Dumont, W.

AU - Kremer, A.

PY - 2009/5/20

Y1 - 2009/5/20

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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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