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- Title
Synthesis of α-Nitro- α-diazocarbonyl Derivatives and Their Applications in the Cyclopropanation of Alkenes and in OH Insertion Reactions.
- Authors
Charette, André B.; Wurz, Ryan P.; Ollevier, Thierry
- 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 OH insertion reaction of the metalcarbene complex derived from the α-nitro- α-diazocarbonyl reagent afforded the corresponding novel α-nitro- α-alkoxy carbonyl derivatives.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 12, p4468
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200290023