Organocatalyzed Asymmetric Conjugate Addition of Heteroaryl and Aryl Trifluoroborates: a Synthetic Strategy for Discoipyrrole D

被引：69
作者：
Shih, Jiun-Le [1 ]
Nguyen, Thien S. [1 ]
May, Jeremy A. [1 ]
机构：
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 34期
关键词：
bis-aryl stereocenters; enantioselective catalysis; heterocycles; organocatalysis; trifluoroborate salts; CROSS-COUPLING REACTIONS; FRIEDEL-CRAFTS ALKYLATIONS; ENANTIOSELECTIVE SYNTHESIS; ALKENYLBORONIC ACIDS; STEREOGENIC CENTERS; BORONIC ESTERS; ENONES; INHIBITORS; KETONES; SALTS;
D O I：
10.1002/anie.201503528
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Bis-heteroaryl or bis-aryl stereocenters were formed by an organocatalytic enantioselective conjugate addition using the respective trifluoroborate salts as nucleophiles. Control studies suggested that fluoride dissociation is necessary in the anhydrous conditions. This strategy is applicable to the synthesis of discoipyrrole D, an inhibitor of BR5 fibroblast migration.
引用
收藏
页码：9931 / 9935
页数：5
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