Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by the Mannich-Type Reaction

Ke-Qiang Hou; Feng Zhou; Xue-Ping Chen; Yang Ge; Albert S C Chan; Xiao-Feng Xiong

doi:10.1021/acs.joc.0c00981

Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by the Mannich-Type Reaction

J Org Chem. 2020 Aug 7;85(15):9661-9671. doi: 10.1021/acs.joc.0c00981. Epub 2020 Jul 10.

Authors

Ke-Qiang Hou¹, Feng Zhou¹, Xue-Ping Chen¹, Yang Ge¹, Albert S C Chan¹, Xiao-Feng Xiong¹

Affiliation

¹ Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.

PMID: 32603113
DOI: 10.1021/acs.joc.0c00981

Abstract

The catalytic asymmetric Mannich-type reaction of 3-hydroxy/3-aminooxindoles with 2-aminoacrylates to afford oxindole-derived acyclic amino acid derivatives bearing vicinal tetrasubstituted stereocenters is reported. (DHQ)₂PHAL (4g) and quinine-derived squaramide (4d) were identified as efficient catalysts. Transformations of the Mannich-type reaction products highlight the utility of this synthetic strategy.

Publication types

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