Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

被引：42

作者：

Davis, Tyler A.

Danneman, Michael W.

Johnston, Jeffrey N. ^{[1
]}

机构：

[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 45期

关键词：

AZA-HENRY REACTION; ENANTIOSELECTIVE SYNTHESIS; NITRO-GROUP; THIOUREA; HYDROGEN; ORGANOCATALYST; REPLACEMENT; ACTIVATION; REACTIVITY; PROGRESS;

D O I：

10.1039/c2cc32225k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.

引用

收藏

页码：5578 / 5580

页数：3

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