A low cost, efficient, metal-free highly stereoselective reduction of ketimines to chiral amines was developed. Different imines bearing a very cheap and removable chiral auxiliary were reduced simply by trichlorosilane in the presence of N,N-dimethyl-formamide, often in quantitative yield and complete control of the absolute stereochemistry, to afford highly enantiomerically enriched amines.

A convenient, highly stereoselective, metal-free synthesis of chiral amines / S. Guizzetti, M. Benaglia, C. Biaggi, G. Celentano. - In: SYNLETT. - ISSN 0936-5214. - 2010:1(2010), pp. 134-136. [10.1055/s-0029-1218541]

A convenient, highly stereoselective, metal-free synthesis of chiral amines

S. Guizzetti
Primo
;
M. Benaglia
Secondo
;
C. Biaggi
Penultimo
;
G. Celentano
Ultimo
2010

Abstract

A low cost, efficient, metal-free highly stereoselective reduction of ketimines to chiral amines was developed. Different imines bearing a very cheap and removable chiral auxiliary were reduced simply by trichlorosilane in the presence of N,N-dimethyl-formamide, often in quantitative yield and complete control of the absolute stereochemistry, to afford highly enantiomerically enriched amines.
Chiral amine; Chiral auxiliary; Imine reduction; Lewis base; Trichlorosilane
Settore CHIM/06 - Chimica Organica
2010
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/143446
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