Interrupted Michael Reaction: Sulfophosphinoylation of α,β-Unsaturated Ketones Catalyzed by Phosphine

被引：1

作者：

Wei, Xiao-Hong ^{[1
]}

Xue, Ya-Wen ^{[1
]}

Liu, Xuan ^{[1
]}

Wang, Xiao-Hong ^{[1
]}

Wang, Yan-Bin ^{[1
]}

Su, Qiong ^{[1
]}

机构：

[1] Northwest Minzu Univ, Coll Chem Engn, Key Lab Environm Friendly Composite Mat, Key Lab Util Environm Friendly Composite Mat & Bio, Lanzhou 730030, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期

基金：

中国国家自然科学基金;

关键词：

MORITA-BAYLIS-HILLMAN; 4+1 ANNULATION; C BOND; CARBONATES; OXIDES; CONSTRUCTION; ALLENES; ACCESS; ACID; 3-NITROINDOLES;

D O I：

10.1021/acs.joc.4c01860

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for phosphine-catalyzed sulfophosphinoylation of alpha,beta-unsaturated ketones for synthesis allylic organophosphorus compounds has been reported, in which alpha,beta-unsaturated compounds acting as zwitterions react with electrophiles and nucleophiles to form a C-P bond and a C-O bond and obtain allylic organophosphorus with high regio- and stereoselectivity in moderate to excellent yields.

引用

页码：16564 / 16570

页数：7

共 50 条

[1] Direct Asymmetric Michael Reaction of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Two Secondary Amine Catalysts [J].

Hayashi, Yujiro ;

Umekubo, Nariyoshi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) :1958-1962

[2] Enantioselective organocatalytic phospha-Michael reaction of α,β-unsaturated ketones [J].

Wen, Shigang ;

Li, Pengfei ;

Wu, Haibo ;

Yu, Feng ;

Liang, Xinmiao ;

Ye, Jinxing .

CHEMICAL COMMUNICATIONS, 2010, 46 (26) :4806-4808

[3] Enantioselective phospha-Michael reaction of diethyl phosphonate with exocyclic α,β-unsaturated benzocyclic ketones catalyzed by a dinuclear zinc-AzePhenol catalyst [J].

Shao, Na ;

Luo, Yong-Yang ;

Lu, Hui-Jie ;

Hua, Yuan-Zhao ;

Wang, Min-Can .

TETRAHEDRON, 2018, 74 (17) :2130-2142

[4] Magnesium-Catalyzed Asymmetric Thia-Michael Addition to α,β-Unsaturated Ketones [J].

Jaszczewska-Adamczak, Joanna A. ;

Baczewska, Paulina ;

Bujok, Robert ;

Mlynarski, Jacek .

ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (06) :1412-1421

[5] Asymmetric vinylogous Michael reaction of α,β-unsaturated ketones with γ-butenolide under multifunctional catalysis [J].

Huang, Huicai ;

Yu, Feng ;

Jin, Zhichao ;

Li, Wenjun ;

Wu, Wenbin ;

Liang, Xinmiao ;

Ye, Jinxing .

CHEMICAL COMMUNICATIONS, 2010, 46 (32) :5957-5959

[6] Phosphine-catalyzed regioselective Michael addition to allenoates [J].

Gandi, Vasudeva Rao ;

Lu, Yixin .

CHEMICAL COMMUNICATIONS, 2015, 51 (90) :16188-16190

[7] Phosphine-catalyzed reaction of cyclopropenones with water: divergent synthesis of highly functionalized γ-butenolides, trisubstituted α,β-unsaturated acids and anhydride [J].

Li, Fujuan ;

Yang, Danna ;

Qu, Hongyan ;

Zhu, Mingqi ;

Zheng, Suqing .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (23) :5582-5589

[8] Asymmetric Michael Reaction of Malononitrile and α,β-Unsaturated Aldehydes Catalyzed by Diarylprolinol Silyl Ether [J].

Hayashi, Yujiro ;

Hatano, Yutaro ;

Mori, Naoki .

SYNLETT, 2022, 33 (18) :1831-1836

[9] An organocatalytic asymmetric double Michael cascade reaction of unsaturated ketones and unsaturated pyrazolones: highly efficient synthesis of spiropyrazolone derivatives [J].

Liang, Jinyan ;

Chen, Qiao ;

Liu, Luping ;

Jiang, Xianxing ;

Wang, Rui .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (09) :1441-1445

[10] Chiral Phosphine Catalyzed Asymmetric Michael Addition of Oxindoles [J].

Zhong, Fangrui ;

Dou, Xiaowei ;

Han, Xiaoyu ;

Yao, Weijun ;

Zhu, Qiang ;

Meng, Yuezhong ;

Lu, Yixin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (03) :943-947

← 1 2 3 4 5 →