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Asymmetric Conjugate Addition of Phosphonates to Enones Using Cinchona-Diaminomethylenemalononitrile Organocatalysts

Ryoga Arai, Shin-ichi Hirashima, Tatsuki Nakano, Masahiro Kawada, Hiroshi Akutsu, Kosuke Nakashima and Tsuyoshi Miura*

*Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan, Email: tmiuratoyaku.ac.jp

R. Arai, S.-i. Hirashima, T. Nakano, M. Kawada, H. Akutsu, K. Nakashima, T. Miura, J. Org. Chem., 2020, 85, 3872-3878.

DOI: 10.1021/acs.joc.9b02553 (free Supporting Information)



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Abstract

A diaminomethylenemalononitrile catalyzes an asymmetric 1,4-addition of phosphonates to trans-crotonophenone and chalcone derivatives to provide chiral γ-ketophosphonates in high yields with excellent enantioselectivities.

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proposed transition-states



Key Words

phosphonates, organocatalysis, Michael addition


ID: J42-Y2020