Chiral Primary Amine Catalyzed Asymmetric Michael Addition of Malononitrile to α‑Substituted Vinyl Ketone

The first efficient
and highly enantioselective Michael addition–protonation
reaction of malononitriles to α-substituted vinyl ketones has
been developed by using a chiral primary amine as the organocatalyst.
With a Hantzsch ester as the hydride source, an enantioselective tandem
reduction, Michael addition–protonation reaction of benzylidene­malono­nitrile
has also been achieved with good yields and high enantioselectivities.

本研究首次开发了以手性伯胺（chiral primary amine）为有机催化剂（organocatalyst）的高效高对映选择性丙二腈（malononitriles）与α-取代乙烯基酮（α-substituted vinyl ketones）间的迈克尔加成-质子化反应。以汉斯酯（Hantzsch ester）作为氢源（hydride source），本研究同时实现了亚苄基丙二腈（benzylidene malononitrile）的对映选择性串联还原-迈克尔加成-质子化反应，产物收率优良且对映选择性优异。