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
收藏
页码：601 / 608
页数：8
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