Issue 66, 2019

A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides

Abstract

A novel tandem intermolecular ammonium ylide formation/intramolecular Mannich-type [5+1] cyclization reaction of aryl diazoacetates and ortho-aminophenyl imine derivatives was developed. The reaction provides an efficient methodology for direct synthesis of diverse trisubstituted tetrahydroquinoxalines bearing a quaternary stereogenic carbon center in moderate to good yields with excellent diastereoselectivity. This process features high efficiency, mild reaction conditions, and high stereoselectivity.

Graphical abstract: A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides

Supplementary files

Article information

Article type
Communication
Submitted
26 Jun 2019
Accepted
23 Jul 2019
First published
24 Jul 2019

Chem. Commun., 2019,55, 9809-9812

A highly diastereoselective [5+1] annulation to 2,2,3-trisubstituted tetrahydroquinoxalines via intramolecular Mannich-type trapping of ammonium ylides

X. Guan, M. Tang, Z. Liu and W. Hu, Chem. Commun., 2019, 55, 9809 DOI: 10.1039/C9CC04890A

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