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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*

*Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany, Email:

C. Sämann, P. Knochel, Synthesis, 2013, 45, 1870-1876.

DOI: 10.1055/s-0033-1338415

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Substituted allylic zinc reagents, prepared via direct metal insertion in substituted allylic halides, react readily with a broad range of acid chlorides and chloroformates to yield the corresponding α-substituted β,γ-unsaturated ketones and esters in high yield and perfect regioselectivity.

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Key Words

organozinc reagents, addition, ketones, esters, insertion, allylic halides

ID: J66-Y2013