New, Readily Available Organocatalysts for the Enantioselective Reduction of α-Imino- and β-Imino Esters

Abstract Novel metal-free, readily available chiral catalytic systems for the enantioselective reduction of keto imines are reported. Different β-imino esters were reduced by trichlorosilane in the presence of 10 mol% of a chiral Lewis base easily obtained in one step only from prolinol, in high yie...

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Bibliographic Details
Published in:Synlett 2011-05, Vol.2011 (8), p.1085-1088
Main Authors: Bonsignore, Martina, Benaglia, Maurizio, Annunziata, Rita, Celentano, Giuseppe
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
Kinetics and mechanisms
letter
Organic chemistry
Reactivity and mechanisms
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Abstract Novel metal-free, readily available chiral catalytic systems for the enantioselective reduction of keto imines are reported. Different β-imino esters were reduced by trichlorosilane in the presence of 10 mol% of a chiral Lewis base easily obtained in one step only from prolinol, in high yields and in up to 85% enantioselectivity; imines bearing an inexpensive and removable chiral auxiliary, were reduced with complete control of the absolute stereochemistry. The methodology was successfully extended to the stereoselective synthesis of α-amino esters.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0030-1259941