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Synthesis of α-Nitro-α-diazocarbonyl Derivatives and Their Applications in the Cyclopropanation of Alkenes and in OH Insertion Reactions

✍ Scribed by André B. Charette; Ryan P. Wurz; Thierry Ollevier

Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
193 KB
Volume
85
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A facile and highly efficient method for the preparation of α‐nitro‐α‐diazocarbonyl derivatives by a diazo‐transfer reaction involving (trifluoromethyl)sulfonyl azide has been developed. These substrates undergo a rhodium‐catalyzed cyclopropanation reaction with a variety of alkenes. A systematic study of the reaction indicated that the diastereoselectivity of the cyclopropanation could be effectively controlled through the modification of the steric bulk of the diazo reagent. A novel OH insertion reaction of the metalcarbene complex derived from the α‐nitro‐α‐diazocarbonyl reagent afforded the corresponding novel α‐nitro‐α‐alkoxy carbonyl derivatives.

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