Diastereoselective Bromination of Compounds Bearing a Cyclohex-3-enol Moiety: Application to the Enantioselective Synthesis of (1R)-cis-Deltamethrinic Acid

(1R)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.

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Bibliographic Details
Published in:Journal of organic chemistry 2008-12, Vol.73 (24), p.9795-9797
Main Authors: Krief, Alain, Jeanmart, Stephane, Kremer, Adrian
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Description
Summary:(1R)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo8022507