A Stereospecific Palladium-Catalyzed Route to Monoalkyl Diazenes for Mild Allylic Reduction

Authors


  • M.M. is a Beckman Young Investigator and a Sloan Research Fellow. O.K.A is grateful for a Merck graduate fellowship. We acknowledge financial support by the NSF (547905), AstraZeneca, Amgen, Eli Lilly, GlaxoSmithKline, Merck Research Laboratories, and Boehringer Ingelheim Pharmaceutical Inc.

Abstract

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One step beyond: The first single-step stereospecific transition-metal-catalyzed conversion of allylic electrophiles into monoalkyl diazenes is described. This synthesis of allylic monoalkyl diazenes offers a new strategy for asymmetric synthesis by the reduction of optically active substrates or the use of chiral catalyst systems. Sensitive substrates are reduced in a highly selective manner. Ar=2-NO2C6H4.

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