A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

Takuya Kanemitsu; Atsushi Umehara; Rieko Haneji; Kazuhiro Nagata; Takashi Itoh

doi:10.1016/j.tet.2012.03.035

A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

Takuya Kanemitsu, Atsushi Umehara, Rieko Haneji, Kazuhiro Nagata, Takashi Itoh

LIF - Molecular and Chemical Life Science

Showa University

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee).

Original language	English
Pages (from-to)	3893-3898
Number of pages	6
Journal	Tetrahedron
Volume	68
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2012.03.035
Publication status	Published - 2012 May 20

Keywords

Amines
Asymmetric synthesis
Lewis bases
Organocatalysis
Reduction

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10.1016/j.tet.2012.03.035

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title = "A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant",

abstract = "A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the corresponding amines in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee).",

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AU - Umehara, Atsushi

AU - Haneji, Rieko

AU - Nagata, Kazuhiro

AU - Itoh, Takashi

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KW - Amines

KW - Asymmetric synthesis

KW - Lewis bases

KW - Organocatalysis

KW - Reduction

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A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

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Keywords

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