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

被引：8

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

共 50 条

[31] Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes
Duan, Cong
Ye, Ling
Xu, Wenqin
Li, Xinying
Chen, Feng
Zhao, Zhigang
Li, Xuefeng
CHINESE CHEMICAL LETTERS, 2018, 29 (08) : 1273 - 1276
[32] 1,6-Conjugate sulfonylation of para-quinone methides: An expedient approach to unsymmetrical gem-diarylmethyl sulfones
Guan, Xiao-Yu
Zhang, Liang-Dong
You, Peng-Sheng
Liu, Sheng-Shu
Liu, Zhang-Qin
TETRAHEDRON LETTERS, 2019, 60 (03) : 244 - 247
[33] Solvent-free 1,6-conjugate arylation of para-quinone methides: A greener approach to unsymmetrical triarylmethanes
Hu, Yu
Tang, Min
Chen, Jia-Xuan
Wei, Shi-Qian
Tian, Yi
Zhang, Liang-Dong
Liu, Zhang-Qin
JOURNAL OF SAUDI CHEMICAL SOCIETY, 2021, 25 (09)
[34] 1,6-Conjugate Addition of 1,3-Dicarbonyl Compounds to para-Quinone Methides Enabled by Noncovalent N-Heterocyclic Carbene Catalysis
Santra, Surojit
Porey, Arka
Guin, Joyram
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (02) : 477 - 486
[35] Enantioselective Synthesis of Triarylmethanes via Organocatalytic 1,6-Addition of Arylboronic Acids to Para-Quinone Methides
Huang, Gong-Bin
Huang, Wei-Hua
Guo, Jing
Xu, Dong-Liang
Qu, Xiao-Chen
Zhai, Pei-Hong
Zheng, Xiu-Hua
Weng, Jiang
Lu, Gui
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1241 - 1246
[36] Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to para-Quinone Methides
Ali, Amjad
Jajoria, Raveena
Harit, Harish K.
Singh, Ravi P.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (08): : 5213 - 5228
[37] Bis(amino)cyclopropenylidene-Catalyzed 1,6-Conjugate Addition of Aromatic Aldehydes to para-Quinone Methides: Expedient Access to α,α′-Diarylated Ketones
Ramanjaneyulu, Bandaru T.
Mahesh, Sriram
Anand, Ramasamy Vijaya
ORGANIC LETTERS, 2015, 17 (16) : 3952 - 3955
[38] Metal-Free Regioselective 1,6-Conjugate Addition of Sulfide to para-Quinone Methides: Simple Access to E-Selective Thiaoxacyclophanes
Kotha, Sambasivarao
Gupta, Naveen K.
Solanke, Balaji U.
CHEMISTRYSELECT, 2023, 8 (34):
[39] Asymmetric Organocatalytic 1,6-Conjugate Addition of Aldehydes to Dienic Sulfones
Murphy, John J.
Quintard, Adrien
McArdle, Patrick
Alexakis, Alexandre
Stephens, John C.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5095 - 5098
[40] Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides
Chen, Min
Sun, Jianwei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) : 4583 - 4587

← 1 2 3 4 5 →