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Water‐Compatible Hydrogen‐Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza‐Henry Reaction
Author(s) -
CruzAcosta Fabio,
de Armas Pedro,
GarcíaTellado Fernando
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303448
Subject(s) - squaramide , stereoselectivity , catalysis , chemistry , combinatorial chemistry , thiourea , enantiomer , scalability , hydrogen bond , molecule , computer science , enantioselective synthesis , stereochemistry , organic chemistry , organocatalysis , database
H‐bond catalysis : The first example of a stereoselective multicomponent aza‐Henry reaction catalyzed by a combination of a chiral H‐bond donor organic molecule (thiourea‐ or squaramide‐containing catalyst) and a Lewis base (tertiary amine) in the presence of water is described (see scheme). Each family of catalysts delivers the β‐nitroamine derivative with complementary enantioselectivity, allowing for the selective access of two enantiomeric series of these building blocks in an efficient, instrumentally simple, and scalable manner.