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Synthesis 2013; 45(13): 1870-1876
DOI: 10.1055/s-0033-1338415
DOI: 10.1055/s-0033-1338415
paper
A Convenient Synthesis of α-Substituted β,γ-Unsaturated Ketones and Esters via the Direct Addition of Substituted Allylic Zinc Reagents Prepared by Direct Insertion
Further Information
Publication History
Received: 20 February 2013
Accepted after revision: 25 March 2013
Publication Date:
30 April 2013 (online)
Dedicated to Professor Scott E. Denmark on the occasion of his 60th birthday
Abstract
A practical and convenient procedure for the synthesis of α-substituted β,γ-unsaturated ketones and esters has been developed. Substituted allylic zinc reagents, prepared via direct metal insertion in substituted allylic halides, react readily with a broad range of acid chlorides and chloroformates furnishing the corresponding α-substituted β,γ-unsaturated ketones and esters in high yield and perfect regioselectivity.
Key words
organozinc reagents - addition - unsaturated ketones and esters - insertion - allylic halidesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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- 22 The reaction has also been carried out without separating the allylic zinc species from the excess of zinc powder with an insignificant loss in yield.
For allylmetal additions, see:
For reviews, see:
For reviews, see: