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Asymmetric Organocatalysis with Novel Chiral Thiourea Derivatives: Bifunctional Catalysts for the Strecker and Nitro‐Michael Reactions
Author(s) -
Tsogoeva Svetlana B.,
Yalalov Denis A.,
Hateley Martin J.,
Weckbecker Christoph,
Huthmacher Klaus
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500420
Subject(s) - chemistry , bifunctional , thiourea , organocatalysis , michael reaction , nitro , enantioselective synthesis , moiety , strecker amino acid synthesis , organic chemistry , imidazole , catalysis , combinatorial chemistry , alkyl
Novel bifunctional organocatalysts bearing both a thiourea moiety and an imidazole group on a chiral scaffold were synthesized and applied to the Strecker synthesis and nitro‐Michael reaction. The addition of acetone to nitroolefins in the presence of these novel bifunctional organocatalysts gave enantioselectivities (up to 87 % ee ) that are superior to those generated by the proline and/or homo‐proline tetrazole catalysts described in the literature. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)