Catalytic asymmetric synthesis of cyclopropanecarboxylic acids: an application of chiral copper carbenoid reaction
Year: 1985
Type: article
Abstract: Reaction of alkyl diazoacetate with an olefin catalyzed by a chiral copper complex gives an optically active alkyl cyclopropanecarboxylate.This chiral copper carbenoid reaction was successfully applied to the synthesis of industrially valuable cyclopropanecarboxylic acids: (÷)-trans-chrysanthem ic acid, (÷)-cis-permethrinic acid and (+)-2,2-dimethylcyclopropanecarboxylic acid.A series of effective catalysts, chiral Schiff base-copper complexes, was prepared starting with an optically active a-amino acid to achieve more than 90% e.e. of the products.The chirality of the products was correlated with that of the catalyst on the basis of metallacyclobutane intermediates.
Source: Pure and Applied Chemistry
Author: Tadatoshi Aratani
Institution: Sumitomo Chemical (Japan)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2111098227