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
收藏
页码：9332 / 9342
页数：11
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