Synthesis of -Nitro--diazocarbonyl Derivatives and Their Applications in the Cyclopropanation of Alkenes and in OH Insertion Reactions
2002; Wiley; Volume: 85; Issue: 12 Linguagem: Inglês
10.1002/hlca.200290023
ISSN1522-2675
AutoresAndré B. Charette, Ryan P. Wurz, Thierry Ollevier,
Tópico(s)Catalytic C–H Functionalization Methods
ResumoAbstract 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.
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