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

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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

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Publication details

The article was received on 29 Jun 2017, accepted on 23 Aug 2017 and first published on 24 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00531H
Citation: Org. Chem. Front., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7QO00531H

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