Enantioselective Organocatalytic Construction of Spiroindane Derivatives by Intramolecular Friedel-Crafts-Type 1,4-Addition

被引：33
|
作者：
Yoshida, Keisuke [1 ]
Itatsu, Yukihiro [1 ]
Fujino, Yuta [1 ]
Inoue, Hiroki [1 ]
Takao, Ken-ichi [1 ]
机构：
[1] Keio Univ, Dept Appl Chem, Kohoku Ku, Hiyoshi, Yokohama, Kanagawa 2238522, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 23期
关键词：
asymmetric catalysis; cyclization; natural products; organocatalysis; Spiro compounds; ALPHA; BETA-UNSATURATED ALDEHYDES; CANNABISPIRENONE-B; NATURAL-PRODUCTS; ALKYLATION; INDOLES; CATALYSIS; SPIROLACTONIZATION; NAPHTHOLS; CASCADE; PHENOLS;
D O I：
10.1002/anie.201601683
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The highly enantioselective organocatalytic construction of spiroindanes containing an all -carbon quaternary stereocenter by intramolecular Friedel Crafts-type 1,4-addition is described. The reaction was catalyzed by a cinchonidine-based primary amine and accelerated by water and pbromophenol. A variety of spiro compounds containing quaternary stereocenters were obtained with excellent enantioselectivity (up to 95 % ee). The reaction was applied to the asymmetric formal synthesis of the spirocyclic natural products (-)-cunnubispt-1 ones A and B.
引用
收藏
页码：6734 / 6738
页数：5
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