[reaction: see text] The first organocatalytic and asymmetric direct vinylogous Michael reaction that employs the electron-deficient vinyl malononitriles as the nucleophilic species has been reported. The novel transformations exhibit exclusive gamma-selectivity and high diastereo- and enantioselectivity in the addition to nitroolefins, which give the multifunctional products with two vicinal chiral centers.
The highly enantioselective Michael addition of malononitrile to acyclic and cyclic alpha,beta-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83-97% ee).
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