Synthesis of Highly Enantioenriched C-Tertiary Amines From Boronic Esters: Application to the Synthesis of Igmesine

被引：62

作者：

Bagutski, Viktor ^{[1
]}

Elford, Tim G. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

azides; boronic esters; C-tertiary amines; quaternary stereocenters; trifluoroborates; ASYMMETRIC STRECKER REACTION; HIGH ENANTIOMERIC PURITIES; ENANTIOSELECTIVE SYNTHESIS; QUATERNARY STEREOCENTERS; SECONDARY-AMINES; STEREOGENIC CENTERS; MANNICH REACTIONS; CHIRAL SYNTHESIS; SIGMA-LIGAND; KETIMINES;

D O I：

10.1002/anie.201006037

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Better than all the rest: Tertiary boronic esters, readily available using the lithiation-borylation reaction, have been converted into tertiary alkylamines in very high ee. The work has been applied to a short, modular, and fully stereocontrolled synthesis of the pharmaceutical igmesine and chiral 2,2-disubstituted piperidines. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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收藏

页码：1080 / 1083

页数：4

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