Enantioselective Synthesis of Highly Substituted Chromans by a Zinc(II)-Catalyzed Tandem Friedel-Crafts Alkylation/Michael Addition Reaction

被引：11

作者：

Li, Chao ^{[1
]}

Liu, Feng-Lei ^{[1
]}

Zou, You-Quan ^{[1
]}

Lu, Liang-Qiu ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 05期

基金：

美国国家科学基金会;

关键词：

tandem reaction; Friedel-Crafts alkylation; 1-methylindole; chroman; nitroolefin enoate; CATALYTIC ASYMMETRIC-SYNTHESIS; CHIRAL BIS(OXAZOLINE) LIGANDS; OXAZOLINE-CONTAINING LIGANDS; CASCADE REACTIONS; VITAMIN-E; BIOMIMETIC CYCLIZATION; BRONSTED ACIDS; MICHAEL; HETEROCYCLES; CYCLOADDITION;

D O I：

10.1055/s-0032-1318200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective tandem Friedel-Crafts alkylation/Michael addition reaction of 1-methylindoles with nitroolefin enoates catalyzed by a chiral tridentate bisoxazoline-Zn(II) complex has been described. This method provides an efficient route to highly substituted chromans in good isolated yields with high stereoselectivities (up to 95: 5 dr and 91% ee).

引用

页码：601 / 608

页数：8

共 89 条

[1] Tandem catalytic asymmetric Friedel-Crafts/Henry reaction: Control of three contiguous acyclic stereocenters [J].