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Synthesis of γ-amino alcohols from aldehydes, enamines, and trichlorosilane using Lewis base catalysts

Author:
Kashiwagi, Takeru, Kotani, Shunsuke, Sugiura, Masaharu, Nakajima, Makoto
Source:
Tetrahedron 2011 v.67 no.2 pp. 531-539
ISSN:
0040-4020
Subject:
alcohols, aldehydes, catalysts, catalytic activity, chemical reactions, diastereomers, enantiomers, models
Abstract:
The reaction of aldehydes, enamines, and trichlorosilane in the presence of a Lewis base catalyst, particularly N-methylpyrrolidinone and DMF, affords γ-amino alcohols with a high diastereoselectivity. The method consists of C–C bond formation between an aldehyde and an enamine, and a subsequent intramolecular reduction of the resulting iminium ion intermediate. In most cases, one diastereomer is exclusively generated, and we propose a transition state model for the intramolecular reduction of the iminium ion intermediate. Enamines, prepared beforehand from the corresponding ketone and amine, can be used in the reaction without purification. Furthermore, enantioselective catalysis using a chiral Lewis base catalyst is possible, although the enantioselectivity is modest. The current tandem method offers the first, concise synthetic method of γ-amino alcohols from aldehydes and enamines.
Agid:
1093359