Asymmetric Organocatalysis with Novel Chiral Thiourea Derivatives: Bifunctional Catalysts for the Strecker and Nitro-Michael Reactions

• Published in: European Journal of Organic Chemistry Vol. 2005; no. 23; pp. 4995 - 5000
• Main Authors: Tsogoeva, Svetlana B., Yalalov, Denis A., Hateley, Martin J., Weckbecker, Christoph, Huthmacher, Klaus
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.12.2005; WILEY‐VCH Verlag; Wiley
• Subjects: Asymmetric catalysis; Bifunctional organocatalysts; Chemistry; Chemistry, Organic; Chiral thioureas; Michael addition; Physical Sciences; Science & Technology; Strecker synthesis; Michael addition; MANNICH; bifunctional organocatalysts; BAYLIS-HILLMAN REACTION; chiral thioureas; ALDOL REACTIONS; ALDEHYDES; asymmetric catalysis; DYNAMIC KINETIC RESOLUTION; AZLACTONES; KETONES; ENANTIOSELECTIVE CONJUGATE ADDITION; NITROOLEFINS; Strecker synthesis; OLEFINS
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200500420

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)