Asymmetric Construction of 3,3-Disubstituted Oxindoles Bearing Vicinal Quaternary-Tertiary Carbon Stereocenters Catalyzed by a Chiral-at-Rhodium Complex

被引：23
|
作者：
Lin, Huihua [1 ,2 ]
Zhou, Zijun [1 ,2 ]
Cai, Jun [1 ,2 ]
Han, Bowen [1 ,2 ]
Gong, Lei [1 ,2 ]
Meggers, Eric [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Dept Biol Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[3] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 12期
基金：
中国国家自然科学基金;
关键词：
ISATIN-DERIVED KETIMINES; ALPHA; BETA-UNSATURATED 2-ACYL IMIDAZOLES; VINYLOGOUS MANNICH REACTION; N-BOC KETIMINES; ENANTIOSELECTIVE CONJUGATE ADDITION; METAL RH(III) COMPLEX; 3-SUBSTITUTED OXINDOLES; NATURAL-PRODUCTS; TETRASUBSTITUTED STEREOCENTERS; PHOTOREDOX CATALYSIS;
D O I：
10.1021/acs.joc.7b00793
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly diastereo- and enantioselective synthesis of 3,3-disubstituted oxindoles bearing vicinal quaternary tertiary carbon centers is enabled by a chiral-at-rhodium Lewis acid catalyst starting from isatin N-protected ketimines and 2-acyl imidazoles. The excellent results with 93-99% yields, diastereoseJectivities of 43:1 to >200:1, and high enantioselectivities of 98.4 to >99% confirm the potential of bis-cyclometalated rhodium catalysts for the development of effective asymmetric transformations.
引用
收藏
页码：6457 / 6467
页数：11
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