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 / D. Petruzziello; A. Gualandi; S. Grilli; P. G. Cozzi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2012:(2012), pp. 6697-6701. [10.1002/ejoc.201201345]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.