Direct and Stereoselective Alkylation of Nitro Derivatives with Activated Alcohols in Trifluoroethanol


  • Dedicated to Professor Dieter Seebach on the occasion of his 75th birthday


Herein we disclose the simple, effective, and practical alkylation of nitroalkanes that takes place with benzylic, benzhydrylic, and propargylic alcohols in trifluoroethanol. A variety of different nitroalkanes bearing functional groups can be used in this SN1-type reaction to afford the desired products in quantitative yields. Different chiral nitro derivatives were submitted to this highly diastereoselective alkylation reaction with selected benzhydrols. A new, effective, and chiral pyrrolidine organocatalyst was prepared by using this methodology.