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Zinc Carbenoid-Mediated Chain Extension: Preparation of α,β-Unsaturated-γ-keto Esters and Amides

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Matthew D. Ronsheim and Charles K. Zercher*

Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824 ckz@christa.unh.edu

J. Org. Chem., 2003, 68 (11), pp 4535–4538

DOI: 10.1021/jo026299g

Publication Date (Web): April 23, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

An efficient one-pot preparation of α,β-unsaturated-γ-keto esters and amides has been developed. A zinc carbenoid-mediated chain extension of a β-dicarbonyl substrate provides access to an intermediate zinc enolate, which is treated sequentially with a halogen and amine base. This method has been applied to a variety of ester and amide starting materials, as well as to amino acid-derived substrates and to a formal synthesis of (R,R)-(−)-pyrenophorin.

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Published In Issue May 30, 2003
Received August 9, 2002

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Zinc Carbenoid-Mediated Chain Extension: Preparation of α,β-Unsaturated-γ-keto Esters and Amides

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

Synthesis of Isohasubanan Alkaloids via Enantioselective Ketone Allylation and Discovery of an Unexpected Rearrangement

Formal Synthesis of (±)-Roseophilin

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