Catalytic Intramolecular Acylsulfenylation of Activated Alkenes: Enantioselective Synthesis of 3,3-Disubstituted Quinoline-2,4-diones

被引：7

作者：

Liu, Wei ^{[1
]}

Zhang, Huan-Qing ^{[1
]}

Liao, Wei-Wei ^{[1
]}

机构：

[1] Jilin Univ, Dept Organ Chem, Coll Chem, 2699 Qianjin St, Changchun 130012, Jilin, Peoples R China

来源：

ACS CATALYSIS | 2018年 / 8卷 / 06期

关键词：

asymmetric catalysis; cyclization; organosulfur compounds; quaternary stereocenter; atom-economy; RADICAL ADDITION/CYCLIZATION CASCADE; MICHAEL-ALDOL REACTIONS; TANDEM REACTION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; CONSTRUCTION; QUINOLINE; CYCLIZATION; ACCESS;

D O I：

10.1021/acscatal.8b01412

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An asymmetric intramolecular acylsulfenylation approach is presented. By combining catalytic amount of chiral amino diether (1S,2S)-L6 and RSLi, a wide range of 3,3-disubstituted quinoline-2,4-dione derivatives incorporating all carbon quaternary stereocenters could be accessed in excellent yields and enantioselectivities in a catalytically atom-economic fashion. The concept relies on an asymmetric SMA/aldol type sequence by employing thioester as a bifunctional carbonyl resource, which enabled the construction of the cyclic scaffolds smoothly.

引用

页码：5460 / +

页数：11

共 44 条

[1] Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols [J].