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Letter

Asymmetric Wolff Rearrangement Reactions with α-Alkylated-α-diazoketones: Stereoselective Synthesis of α-Substituted-β-amino Acid Derivatives^†

Supporting Info

Hua Yang,* Katherine Foster, Corey R. J. Stephenson, William Brown, and Edward Roberts

Department of Chemistry, AstraZeneca R&D Montreal, 7171 Frederick-Banting, St. Laurent, Quebec, Canada H4S 1Z9

Org. Lett., 2000, 2 (14), pp 2177–2179

DOI: 10.1021/ol006146k

Publication Date (Web): June 17, 2000

†

This paper is dedicated to Professor Stephen Hanessian on the occasion of his 65th birthday.

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

, hua.yang@astrazeneca.com

Abstract

Photoinduced asymmetric Wolff rearrangement reactions were performed with α-amino-α‘-methyl-α‘-diazoketones to afford α-methyl-β-amino acid esters with good stereoselectivity. Factors that may influence the stereochemistry were examined, including steric effects and temperature dependence, which had a great impact on the stereochemistry.

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History

Published In Issue July 13, 2000
Received June 1, 2000

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Letter

Asymmetric Wolff Rearrangement Reactions with α-Alkylated-α-diazoketones: Stereoselective Synthesis of α-Substituted-β-amino Acid Derivatives^†