Asymmetric Direct Vinylogous Conjugate Addition of Substituted Furanone Derivatives to Benzoyl Acrylonitrile: Stereoselective Synthesis Toward Bicyclic γ-Lactams

A diaminomethylenemalononitrile organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate additions of α-angelica lactones to benzoyl acrylonitrile derivatives, resulting in the corresponding addition products bearing vicinal tertiary and quaternary stereogenic centers with exce...

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Published in:Organic letters 2021-01, Vol.23 (2), p.480-485
Main Authors: Ishii, Daiki, Hirashima, Shin-Ichi, Nakashima, Kosuke, Akutsu, Hiroshi, Sakai, Takaaki, Matsushima, Yasuyuki, Kawada, Masahiro, Miura, Tsuyoshi
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cited_by cdi_FETCH-LOGICAL-c305t-28cd3bf5e403605c3ce8684a8b1204877a28ad57fe5cce00a687ae43dcafe1dd3
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container_end_page 485
container_issue 2
container_start_page 480
container_title Organic letters
container_volume 23
creator Ishii, Daiki
Hirashima, Shin-Ichi
Nakashima, Kosuke
Akutsu, Hiroshi
Sakai, Takaaki
Matsushima, Yasuyuki
Kawada, Masahiro
Miura, Tsuyoshi
description A diaminomethylenemalononitrile organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate additions of α-angelica lactones to benzoyl acrylonitrile derivatives, resulting in the corresponding addition products bearing vicinal tertiary and quaternary stereogenic centers with excellent enantioselectivities (up to 99% ee). This report is the first successful example of the asymmetric conjugate additions of α-angelica lactone to benzoyl acrylonitriles. The chiral γ,γ-disubstituted γ-butenolides obtained can be readily transformed to the bicyclic γ-lactam derivative as a valuable synthetic intermediate.
doi_str_mv 10.1021/acs.orglett.0c04004
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Asymmetric Direct Vinylogous Conjugate Addition of Substituted Furanone Derivatives to Benzoyl Acrylonitrile: Stereoselective Synthesis Toward Bicyclic γ-Lactams
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