Asymmetric Henry Reaction of Trifluoromethyl Enones with Nitromethane Using a <i>N,N</i>‐Dibenzyl Diaminomethylenemalononitrile Organocatalyst
Masahiro Kawada, Ryo Tsuyusaki, Kosuke Nakashima, Misaki Yamada, Akihiro Kozakai, Yasuyuki Matsushima, Shin‐ichi Hirashima, Tsuyoshi Miura
Abstract
A novel N,N-dibenzyl diaminomethylenemalononitrile organocatalyst efficiently promoted asymmetric Henry reactions of trifluoromethyl enones with nitromethane, affording corresponding highly functionalized products in high yields with excellent enantioselectivities (up to 90% ee). This study is the first to report the successful example of the asymmetric 1,2-additions of nitromethane to trifluoromethyl enones.
Topics & Concepts
NitromethaneTrifluoromethylChemistryNitroaldol reactionOrganocatalysisEnantioselective synthesisOrganic chemistryCatalysisAlkylFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms