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Simple Preparation of α-Diazo Esters

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Douglass F. Taber,* Ritesh B. Sheth, and Pramod V. Joshi

Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716 taberdf@udel.edu

J. Org. Chem., 2005, 70 (7), pp 2851–2854

DOI: 10.1021/jo048011o

Publication Date (Web): February 24, 2005

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

The TiCl₄-mediated reaction of an ester with benzoyl chloride results in high yields of the α-benzoylated ester. Diazo transfer of the benzoylated ester utilizing p-acetoamidobenzenesulfonyl azide affords the α-diazo ester in good yield. Using this simplified procedure, it is easy to prepare gram quantities of α-diazo esters.

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Published In Issue April 01, 2005
Received November 9, 2004

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Simple Preparation of α-Diazo Esters

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Syntheses of Kapakahines B and F

Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes

A Simple Preparation of .alpha.-Diazo Esters

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