Palladium-Catalyzed Highly Stereoselective Dearomative [3

被引：147

作者：

Cheng, Qiang ^{[1
]}

Zhang, Hui-Jun ^{[1
]}

Yue, Wen-Jun ^{[1
]}

You, Shu-Li ^{[1
,2
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Lu, Shanghai 200032, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China

来源：

CHEM | 2017年 / 3卷 / 03期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; ASYMMETRIC DEAROMATIZATION; CYCLOADDITION REACTIONS; (PHOSPHANYLOXAZOLINE)PALLADIUM COMPLEXES; DIASTEREOSELECTIVE SYNTHESIS; PSOROSPERMUM-FEBRIFUGUM; ALLYLIC SUBSTITUTIONS; NMR INVESTIGATIONS; CHIRAL LIGANDS; INDOLES;

D O I：

10.1016/j.chempr.2017.06.015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%-92%), diastereoselectivity (13/1 -> >20/1 dr), and enantioselectivity (75%-95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.

引用

页码：428 / 436

页数：9

共 78 条

[1] XANTHONES AND VISMIONES FROM PSOROSPERMUM-FEBRIFUGUM [J].