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

Christoph Sämann; Paul Knochel

doi:10.1055/s-0033-1338415

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(13): 1870-1876
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

Christoph Sämann

Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany Fax: +49(89)218077680 eMail: paul.knochel@cup.uni-muenchen.de

,

Paul Knochel*

Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstraße 5–13, Haus F, 81377 München, Germany Fax: +49(89)218077680 eMail: paul.knochel@cup.uni-muenchen.de

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Abstract

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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 halides

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Referenzen

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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.

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