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

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

J Org Chem

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

Published: August 2020

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)PHAL () and quinine-derived squaramide () were identified as efficient catalysts. Transformations of the Mannich-type reaction products highlight the utility of this synthetic strategy.

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Source
http://dx.doi.org/10.1021/acs.joc.0c00981DOI Listing

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