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亚胺的高立体选择性无金属催化还原:对映体纯胺以及天然和非天然α-氨基酯的简易合成方法

Highly stereoselective metal-free catalytic reduction of imines: an easy entry to enantiomerically pure amines and natural and unnatural alpha-amino esters.

作者信息

Guizzetti Stefania, Benaglia Maurizio, Rossi Sergio

机构信息

Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Golgi 19, I-20133 Milano, Italy.

出版信息

Org Lett. 2009 Jul 2;11(13):2928-31. doi: 10.1021/ol900945h.

Abstract

A highly efficient catalytic stereoselective ketimine reduction is described. The combination of an inexpensive chiral organocatalyst, easily prepared in a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantiomerically pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters in high yields often with total control of the absolute stereochemistry.

摘要

本文描述了一种高效的催化立体选择性酮亚胺还原反应。一种廉价的手性有机催化剂(可一步轻松制备)与一种非常便宜的可去除手性助剂相结合,使我们能够获得对映体纯的氨基化合物。该方法能够以高收率合成手性仲胺和伯胺以及天然和非天然氨基酯,并且常常能够完全控制绝对立体化学。

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