Asymmetric Direct Vinylogous Conjugate Addition of Substituted Furanone Derivatives to (E)‐ and (Z)‐Benzoyl Acrylonitriles Using Organocatalysts. Issue 5 (16th March 2022)

• Record Type: Journal Article
• Authors: Ishii, Daiki; Hirashima, Shin‐ichi; Akutsu, Hiroshi; Nakashima, Kosuke; Matsushima, Yasuyuki; Sakai, Takaaki; Miura, Tsuyoshi
• Is Part Of: Asian journal of organic chemistry. Volume 11:Issue 5(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-16
• Subjects: α-angelica lactone -- asymmetric reaction -- (Z)-benzoyl acrylonitrile -- conjugate addition -- organocatalyst; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200048
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Diaminomethylenemalononitrile organocatalysts efficiently promoted the asymmetric direct vinylogous conjugate addition of α‐angelica lactone to ( E )‐ and ( Z )‐benzoyl acrylonitrile derivatives. The synthesized products bear vicinal tertiary and quaternary stereogenic centers with excellent enantioselectivities (up to 98% ee). This report is the first successful example of the stereoselective conjugate addition using ( Z )‐benzoyl acrylonitriles as Michael acceptor. Abstract : Diaminomethylenemalononitrile organocatalysts efficiently promoted the asymmetric direct vinylogous conjugate addition of α‐angelica lactone to ( E )‐ and ( Z )‐benzoyl acrylonitrile derivatives, resulting in the corresponding addition products bearing a vicinal tertiary and quaternary stereogenic centers with excellent enantioselectivities (up to 98% ee).