麦基钦型双胺的手性合成。

Chiral Synthesis of McGeachin-Type Bisaminals.

机构信息

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China.

Research Institute of Jilin Petrochemical Company, PetroChina, Jilin, Jilin 132021, China.

出版信息

J Org Chem. 2020 Mar 6;85(5):3709-3716. doi: 10.1021/acs.joc.9b03362. Epub 2020 Feb 12.

DOI:10.1021/acs.joc.9b03362

PMID:31997639

Abstract

Bridged [3.3.1]-bisaminal structures, namely 6,12-epiminodibenzo[,][1,5]diazocines, are herein named McGeachin-type bisaminals. The TsOH-catalyzed chiral synthesis of McGeachin-type bisaminals is first developed by condensation of two molecules of 2-(methylamino)benzaldehyde and one molecule of chiral amines. Two chiral diastereomers are generated simultaneously and are isolated by column chromatography in a total yield of up to 99%. The absolute structure of one stereoisomer was determined by X-ray crystallography.

摘要

桥联[3.3.1]-双亚氨基结构，即 6,12-亚氨基二苯并[,][1,5]二氮杂环辛烷，在此被命名为麦基钦型双亚氨基。首次通过 TsOH 催化的 2-(甲氨基)苯甲醛和手性胺的缩合反应，实现了麦基钦型双亚氨基的手性合成。该反应同时生成了两种手性非对映异构体，并通过柱层析分离，总收率高达 99%。通过 X 射线晶体学确定了一个立体异构体的绝对结构。