Asymmetric Synthesis of Hydrocarbazoles Catalyzed by an Octahedral Chiral-at-Rhodium Lewis Acid

被引：31
|
作者：
Huang, Yong [1 ,2 ]
Song, Liangliang [1 ,2 ]
Gong, Lei [1 ,2 ]
Meggers, Eric [1 ,2 ,3 ]
机构：
[1] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Dept Biol Chem, Xiamen 361005, Peoples R China
[3] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 12期
关键词：
asymmetric catalysis; chiral-at-metal; Diels-Alder; hydrocarbazoles; rhodium; DIELS-ALDER REACTION; METAL-COMPLEXES; FUNCTIONALIZED TETRAHYDROCARBAZOLES; EFFICIENT ROUTE; VISIBLE-LIGHT; 2-VINYLINDOLES; ALKALOIDS; METHYLENEINDOLINONES; QUINODIMETHANES; 3-VINYLINDOLES;
D O I：
10.1002/asia.201500764
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A bis-cyclometalated chiral-at-metal rhodium complex catalyzes the Diels-Alder reaction between N-Boc-protected 3-vinylindoles (Boc = tert-butyloxycarbonyl) and beta-carboxylic ester-substituted alpha,beta-unsaturated 2-acyl imidazoles with good-to-excellent regioselectivity (up to 99:1) and excellent diastereoselectivity (>50:1 d.r.) as well as enantioselectivity (92-99% ee) under optimized conditions. The rhodium catalyst serves as a chiral Lewis acid to activate the 2-acyl imidazole dienophile by two-point binding and overrules the preferred regioselectivity of the uncatalyzed reaction.
引用
收藏
页码：2737 / 2742
页数：6
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