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.

D. Petruzziello, A. Gualandi, S. Grilli, P. G. Cozzi (2012). Direct and Stereoselective Alkylation of Nitro Derivatives with Activated Alcohols in Trifluoroethanol. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 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.
2012
D. Petruzziello, A. Gualandi, S. Grilli, P. G. Cozzi (2012). Direct and Stereoselective Alkylation of Nitro Derivatives with Activated Alcohols in Trifluoroethanol. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 6697-6701 [10.1002/ejoc.201201345].
D. Petruzziello; A. Gualandi; S. Grilli; P. G. Cozzi
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/132211
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 28
  • ???jsp.display-item.citation.isi??? 26
social impact