Asymmetric catalytic [4+3] cycloaddition of ortho-quinone methides with oxiranes

被引：23

作者：

Tan, Qingfa ^{[1
]}

Yu, Han ^{[1
]}

Luo, Yao ^{[1
]}

Chang, Fenzhen ^{[1
]}

Liu, Xiaohua ^{[1
]}

Zhou, Yuqiao ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 24期

基金：

中国国家自然科学基金;

关键词：

BIOSYNTHESIS; ANNULATION; ALKALOIDS;

D O I：

10.1039/d1cc00262g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic enantioselective [4+3] cycloaddition reaction between o-quinone methides and oxiranes was achieved by using a chiral N,N '-dioxide/Tb-III complex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%) with good to excellent diastereo-(up to 94 : 6 dr) and enantioselectivities (up to 97% ee). The topographic steric maps and distribution of the buried volume (% V-Bur) of the catalysts via Cavallo's SambVca 2 tool were collected to effectively represent the chiral pocket of metal complexes of chiral N,N '-dioxides.

引用

页码：3018 / 3021

页数：4

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