Enantioselective Synthesis of β-Amino Esters Bearing a Benzothiazole Moiety via a Mannich-Type Reaction Catalyzed by a Cinchona Alkaloid Derivative

✍ Scribed by Liang Li; Bao-An Song; Pinaki S. Bhadury; Yu-Ping Zhang; De-Yu Hu; Song Yang

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 424 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100351

✦ Synopsis

Abstract

Novel β‐amino esters bearing a bioactive benzothiazole moiety were obtained with high enantioselectivities (up to 95 % ee) through a Mannich‐type reaction of different imines with malonate in the presence of a new chiral cinchona alkaloid thiourea catalyst. Imines derived from both aromatic and heterocyclic aldehydes were found useful in this conversion.