Asymmetric Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides Using [1,2]-Phospha-Brook Rearrangement

被引：13

作者：

Tan, Qingfa ^{[1
]}

Guo, Ning ^{[1
]}

Yang, Linhan ^{[2
]}

Wang, Fei ^{[2
]}

Feng, Xiaoming ^{[1
]}

Liu, Xiaohua ^{[1
]}

机构：

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

[2] Chinese Acad Sci, Chengdu Inst Biol, Ctr Nat Prod Res, Chengdu 610041, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期

基金：

中国国家自然科学基金;

关键词：

ALPHA-KETOESTERS; PHOSPHORUS; DERIVATIVES; ISATINS; IMINES;

D O I：

10.1021/acs.joc.3c00910

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pudovik addition/[1,2]-phospha-Brook rearrangement asan efficienttool for generation of anionic nucleophiles is an attractive strategyfor the construction of C-C bonds in organic synthesis. Herein,we report organocatalytic 1,6-conjugate addition of para-quinone methides utilizing Pudovik addition/[1,2]-phospha-Brookrearrangement. Chiral guanidine-sulfonamide catalyzed the three-componentreaction efficiently, providing biologically active oxindole/biaryl/phosphorus-basedstructures in high yields with excellent diastereo- and enantioselectivities.A possible bifunctional catalytic mode was proposed to elucidate thechiral control of this process.

引用

页码：9332 / 9342

页数：11

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