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Organocatalytic Asymmetric Cyanosilylation of Nitroalkenes
Author(s) -
Bernal Pablo,
Fernández Rosario,
Lassaletta José M.
Publication year - 2010
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.201001107
Subject(s) - thiourea , nitroalkene , bifunctional , cyanide , chemistry , catalysis , bifunctional catalyst , organocatalysis , derivative (finance) , hydrogen bond , organic chemistry , combinatorial chemistry , enantioselective synthesis , molecule , financial economics , economics
New catalyst, new reaction : The unprecedented cyanosilylation of nitroalkenes can be efficiently catalyzed by a bifunctional quinine derivative with tetraalkylammonium cyanide and thiourea moieties. The activation of the nitroalkene by hydrogen bonding to the thiourea, together with the presence of an “active” cyanide, provides a new mode of activation that leads to products in high yields and good selectivities (see scheme).