Sulfonamide Ligands from Chiral Aziridines − Application to the Titanium-Mediated Addition of Diethylzinc to Benzaldehyde

• Published in: European journal of organic chemistry Vol. 2002; no. 18; pp. 3179 - 3188
• Main Authors: Lake, Fredrik, Moberg, Christina
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2002; WILEY‐VCH Verlag; Wiley
• Subjects: aldol reactions; aliphatic-aldehydes; allylic alcohols; Aziridines; bis(halomethyl)zinc reagents; c2-symmetrical disulfonamide; catalytic enantioselective cyclopropanation; Chemistry; Chemistry, Organic; complexes; diels-alder; Diethylzinc; Enantioselective; michael additions; parallel library; Physical Sciences; Science & Technology; Sulfonamides; Titanium; aziridines; diethylzinc; DIELS-ALDER; titanium; COMPLEXES; DIALKYLZINC; sulfonamides; BIS(HALOMETHYL)ZINC REAGENTS; CATALYTIC ENANTIOSELECTIVE CYCLOPROPANATION; PROBES; C2-SYMMETRICAL DISULFONAMIDE; ALLYLIC ALCOHOLS; N-TOSYL; MICHAEL ADDITIONS; enantioselective
• ISSN: 1434-193X; 1099-0690; 1099-0690
• DOI: 10.1002/1099-0690(200209)2002:18<3179::AID-EJOC3179>3.0.CO;2-A

A modular approach was developed for the preparation of chiral, enantiopure sulfonamide ligands with C1, C2, and C3 symmetry by ring opening of chiral N‐sulfonylaziridines with ammonia, primary amines, and diamines. The new ligands were assessed in the titanium‐mediated addition of diethylzinc to benzaldehyde, giving the product with selectivities up to 76% ee. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)