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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Bibliographic Details
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
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04004