Chiral Synthesis of McGeachin-Type Bisaminals

Yang Chen; Siqi Li; Shili Hou; Jiaxi Xu; Zhanhui Yang

doi:10.1021/acs.joc.9b03362

Chiral Synthesis of McGeachin-Type Bisaminals

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

Authors

Yang Chen¹, Siqi Li^{1

2}, Shili Hou³, Jiaxi Xu¹, Zhanhui Yang¹

Affiliations

¹ State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
² Research Institute of Jilin Petrochemical Company, PetroChina, Jilin, Jilin 132021, China.
³ Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin, Guangxi 541004, China.

PMID: 31997639
DOI: 10.1021/acs.joc.9b03362

Abstract

Bridged [3.3.1]-bisaminal structures, namely 6,12-epiminodibenzo[b,f][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.

Publication types

Research Support, Non-U.S. Gov't