Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids

Amrita Das; Kenji Watanabe; Hiroyuki Morimoto; Takashi Ohshima

doi:10.1021/acs.orglett.7b02727

Boronic Acid Accelerated Three-Component Reaction for the Synthesis of α-Sulfanyl-Substituted Indole-3-acetic Acids

Org Lett. 2017 Nov 3;19(21):5794-5797. doi: 10.1021/acs.orglett.7b02727.

Authors

Amrita Das¹, Kenji Watanabe¹, Hiroyuki Morimoto¹, Takashi Ohshima¹

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyushu University , 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.

PMID: 29043814
DOI: 10.1021/acs.orglett.7b02727

Abstract

Boronic acid was used to accelerate a three-component reaction of indoles, thiols, and glyoxylic acids for the synthesis of α-sulfanyl-substituted indole-3-acetic acids. Boronic acid catalysis to activate the α-hydroxy group in α-hydroxycarboxylic acid intermediates and intramolecular assistance by free carboxylic acid were the keys to accelerating the product formation.

Publication types

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