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.

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

PETRUZZIELLO, DIEGO;GUALANDI, ANDREA;GRILLI, STEFANO;COZZI, PIER GIORGIO
2012

Abstract

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.
2012
D. Petruzziello; A. Gualandi; S. Grilli; P. G. Cozzi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/132211
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