期刊
TETRAHEDRON
卷 65, 期 32, 页码 6354-6363出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.06.015
关键词
Pyridine N-oxides; Organocatalysis; Monoterpenes; Allyltrichlorosilane; Epoxide opening
资金
- MIUR (Rome)
The reduction of the carbon-nitrogen double bond is an important transformation. Here we report our studies on a family of chiral organic catalysts able to promote the stereoselective reduction of ketimines with trichlorosilane. The very cheap, metal-free catalysts were easily prepared in one step from commercially available products, namely a chiral aminoalcohol and picolinic acid derivatives. The catalyst structure was extensively modified in a study that allowed to identify an extremely active species, able to promote the reduction on a large variety of substrates with high efficiency (up to 95% ee). A three component methodology has been also developed, where the enantiomerically enriched amine was isolated after performing the reaction by mixing a ketone and an amine in the presence of trichlorosilane and the catalyst. Its synthetic potentiality was demonstrated by employing the present metal-free catalytic procedure in the preparation of (S)-metolachlor, a potent and widely used herbicide. (C) 2009 Elsevier Ltd. All rights reserved.
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