Issue 12, 2017

An enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones and 2-phthalimidoacrylates

Abstract

A highly enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones to 2-phthalimidoacrylates has been developed using a bifunctional tertiary-amine thiourea catalyst. A number of chiral 3-substituted benzothiophen-2-one compounds were obtained with excellent yields (up to 99%) and very good stereoselectivities (up to >19 : 1 dr and up to 92% ee). The reaction was proved to be an efficient strategy for the synthesis of enantioenriched α-amino acid derivatives with 1,3-nonadjacent stereogenic centers.

Graphical abstract: An enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones and 2-phthalimidoacrylates

Supplementary files

Article information

Article type
Research Article
Submitted
29 Jun 2017
Accepted
23 Aug 2017
First published
24 Aug 2017

Org. Chem. Front., 2017,4, 2301-2305

An enantioselective conjugate addition reaction of 3-substituted benzothiophen-2-ones and 2-phthalimidoacrylates

S. Li, E. Zhang, J. Feng and X. Li, Org. Chem. Front., 2017, 4, 2301 DOI: 10.1039/C7QO00531H

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