Pd-Catalyzed Site-Selective Mono-allylic Substitution and Bis-arylation by Directed Allylic C-H Activation: Synthesis of anti-γ-(Aryl,Styryl)-β-hydroxy Acids and Highly Substituted Tetrahydrofurans

被引：28

作者：

Nallasivam, Jothi L. ^{[1
]}

Fernandes, Rodney A. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 40期

关键词：

VINYL-GAMMA-BUTYROLACTONE; HAGENS GLAND LACTONES; BETA-LACTAM ANTIBIOTICS; ARYLBORONIC ACIDS; ENANTIOSELECTIVE SYNTHESIS; GRIGNARD-REAGENTS; COUPLING REACTION; BORONIC ACIDS; ALKYLATION; ARYL;

D O I：

10.1021/jacs.6b06438

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient palladium-catalyzed site-selective arylation of gamma-vinyl-gamma-lactone by aryl boronic acid has been developed. gamma-Vinyl-gamma-lactone la has been contemplated as allyl electrophile donor for allylic arylation via pi-allyl palladium intermediate using 1.5 equiv of aryl boronic acid 2. Using 3.0 equiv of the latter resulted in mono-arylation by allylic substitution and subsequent site-selective second arylation by directed allylic C-H activation giving stereoselectively anti-gamma-(aryl,styryl)-beta-hydroxy acids. Presence of O-2 was crucial for the second arylation via Pd(II) catalysis. Thus, a good synergy of dual catalysis by Pd(0) and Pd(II) was observed. This methodology has been elaborated to synthesize highly substituted tetrahydrofurans including aryl-Hagen's gland lactone analogues via intramolecular iodoetherification.

引用

页码：13238 / 13245

页数：8