Highly Enantioselective Direct Michael Addition of 1H-Benzotriazole to Chalcones Catalyzed by Sc(OTf)3/N,N′-Dioxide Complex

✍ Scribed by Jing Wang; Wentao Wang; Xiaohua Liu; Zongrui Hou; Lili Lin; Xiaoming Feng

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 396 KB
• Volume: 2011
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201100021

✦ Synopsis

Abstract

The N,N′‐dioxide–Sc(OTf)~3~ complex was applied in the asymmetric Michael reaction of 1__H__‐benzotriazole with chalcones to give the corresponding N‐1 products in excellent yields (up to 99 %) with excellent enantioselectivities (up to 99 % ee). Further transformation into other optically active derivatives such as β‐benzotriazolyl ester, alcohol, and amide were also realized with excellent results.