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Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio- and diastereoselective Michael addition reactions

Author:
Farley, Alistair J.M., Jakubec, Pavol, Goldys, Anna M., Dixon, Darren J.
Source:
Tetrahedron 2018
ISSN:
0040-4020
Subject:
chemical reactions, chemical structure, diastereoselectivity, nitroalkenes, urea
Abstract:
Bifunctional iminophosphorane (BIMP) organocatalysts catalyze the enantio- and diastereoselective Michael additions of high pKa cyclic malonamate ester pro-nucleophiles to nitroalkenes with reactivity profiles of up to 3 orders of magnitude greater than tertiary amine bifunctional Brønsted base/(thio)urea organocatalysts. The unrivalled performance of the BIMPs allows reaction times of challenging reactions to be slashed from weeks to minutes and has enabled new flow chemistry applications using polystyrene-supported versions contained within a flow reactor.
Agid:
6130886