Diastereoselective reductive Amination of aryl trifluoromethyl ketones and α-amino esters

被引：51

作者：

Hughes, Greg

Devine, Paul N.

Naber, John R.

O'Shea, Paul D.

Foster, Bruce S.

McKay, Daniel J.

Volante, R. P.

机构：

[1] Merck Frosst Canada Inc, Proc Res, Kirkland, PQ H9H 3L1, Canada

[2] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 11期

关键词：

amines; amino acids; diastereoselectivity; fluorine; reduction;

D O I：

10.1002/anie.200603745

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Reductionist art: Careful choice of the reducing agent in the reductive amination of trifluoromethyl ketones with α-amino esters allows stereoselective access, from the imine formed, to either the R,S or S,S diastereomers of the resulting amino acids. Whereas NaBH4 affords the R,S diastereomers, Zn(BH4)2 affords the S,S diastereomers (see scheme), which can be easily converted into potent cathepsin K inhibitors. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：1839 / 1842

页数：4

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