Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin‐Derived Ketimines1. (7th November 2014)

• Record Type: Journal Article
• Authors: Zhao, Jiannan; Fang, Bing; Luo, Weiwei; Hao, Xiaoyu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
• Is Part Of: Angewandte Chemie. Volume 127:Number 1(2015)
• Page Start: 243
• Page End: 246
• Publication Date: 2014-11-07
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201408730
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A highly enantioselective Mannich reaction of silyl ketene imines with isatin‐derived ketimines has been realized by using a chiral <italic>N</italic>, <italic>N′</italic>‐dioxide/Zn^II catalyst. A variety of β‐amino nitriles containing congested vicinal tetrasubstituted stereocenters were obtained with excellent outcomes (up to 98 % yield, &gt;19:1 d.r. and 99 % <italic>ee</italic>). Based on the experimental investigations, a possible transition state has been proposed to explain the origin of the asymmetric induction.</p> </abstract>