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Communication

Organocatalytic Mitsunobu Reactions

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Tracy Yuen Sze But and Patrick H. Toy*

Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, People's Republic of China

J. Am. Chem. Soc., 2006, 128 (30), pp 9636–9637

DOI: 10.1021/ja063141v

Publication Date (Web): July 6, 2006

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

, phtoy@hku.hk

Abstract

A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those obtained from corresponding stoichiometric reactions. Both primary and secondary alcohols can be used as substrates in this reaction system, with the secondary alcohols affording products with inverted stereochemistry at the carbinol center.

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Published In Issue August 02, 2006
Received May 5, 2006

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Communication

Organocatalytic Mitsunobu Reactions

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Simplification of the Mitsunobu Reaction. Di-p-chlorobenzyl Azodicarboxylate: A New Azodicarboxylate

Use of Sonication for the Coupling of Sterically Hindered Substrates in the Phenolic Mitsunobu Reaction

Mechanistic Study of the Mitsunobu Reaction

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