A novel procedure for the synthesis of epoxides: application of simmons-smith reagents toward epoxidation

摘要

The Simmon-Smith reaction and recent modifica- tions thereof has emerged as a powerful method for the diastereo- and enantioselective cyclopropanation of al- kenes. In view of their effectiveness as cyclopropanating agents, it was surprising that Simmons-Smith reagents had not been exploited further in organic synthesis. Motivated by this, and by our interest in catalytic Asymmetric epoxidation, we initialed a program focused Toward the use of Simmons-Smith reagents for the Synthesis of epoxides, and in this paper we report our Success in achieving this goal (Scheme 1).