Synthesis 2020; 52(24): 3874-3880
DOI: 10.1055/s-0040-1707285
paper

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

Hiroshi Akutsu
,
Kosuke Nakashima
,
Yuta Kanetsuna
,
Masahiro Kawada
,
Shin-ichi Hirashima
,
Tsuyoshi Miura
Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan   eMail: tmiura@toyaku.ac.jp
› Institutsangaben


Abstract

A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

Supporting Information



Publikationsverlauf

Eingereicht: 28. Juli 2020

Angenommen nach Revision: 20. August 2020

Artikel online veröffentlicht:
22. September 2020

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