Palladium-catalyzed 1,4-addition of diarylphosphines to α,β-unsaturated N-acylpyrroles

被引：66

作者：

Du, Dan ^{[2
]}

Duan, Wei-Liang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Shanghai 200237, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 39期

关键词：

P-STEREOGENIC PHOSPHINES; ORGANOCATALYTIC ASYMMETRIC HYDROPHOSPHINATION; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; CHIROGENIC PHOSPHINE; SECONDARY PHOSPHINES; CONJUGATE ADDITION; DIPHENYL PHOSPHITE; ACTIVATED OLEFINS; CHIRAL PHOSPHINES;

D O I：

10.1039/c1cc13785a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly stereoselective asymmetric 1,4-addition of diarylphosphines to alpha,beta-unsaturated N-acylpyrroles catalyzed by a PCP pincer-Pd complex has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (91-99% ee) under mild conditions. The products obtained can be further converted into chiral phosphine-oxazoline ligands.

引用

页码：11101 / 11103

页数：3

共 50 条

[31] Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles [J].

Shockley, Samantha E. ;

Holder, Jeffrey C. ;

Stoltz, Brian M. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (08) :974-981

[32] Copper-Catalyzed 1,4-Addition of a Silicon Nucleophile to Azadienes [J].

Chu, Wen-Dao ;

Wang, Chun-Mei ;

Zhan, Jie ;

Zeng, Ya-Li ;

Liu, Yong ;

Chen, Bo ;

Zhang, Kaiming ;

He, Cheng-Yu ;

Liu, Quan-Zhong .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (16)

[33] Rhodium(I)-catalyzed enantioselective 1,4-addition of nucleophilic silicon [J].

Walter, Christian ;

Froehlich, Roland ;

Oestreich, Martin .

TETRAHEDRON, 2009, 65 (28) :5513-5520

[34] Stereoselective 1,4-Addition of Primary Alcohols to γ-Alkoxy-α,β-unsaturated Esters [J].

Inatomi, Saki ;

Takayanagi, Yuta ;

Watanabe, Kento ;

Toita, Akinori ;

Yamakoshi, Hiroyuki ;

Nakamura, Seiichi .

SYNTHESIS-STUTTGART, 2021, 53 (01) :161-174

[35] Chiral Tetrafluorobenzobarrelenes as Effective Ligands for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboroxines to β,β-Disubstituted α,β-Unsaturated Ketones [J].

Shintani, Ryo ;

Takeda, Momotaro ;

Nishimura, Takahiro ;

Hayashi, Tamio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (23) :3969-3971

[36] 1,4-Addition of aryl boronic acids to α,β-unsaturated ketones catalyzed by a CCC-NHC pincer rhodium complex [J].

Reilly, Sean W. ;

Box, Hannah K. ;

Kuchenbeiser, Glenn R. ;

Rubio, Ramel J. ;

Letko, Christopher S. ;

Cousineau, Kandarpa D. ;

Hollis, T. Keith .

TETRAHEDRON LETTERS, 2014, 55 (49) :6738-6742

[37] Palladium-Catalyzed Asymmetric Addition of Arylboronic Acids to Nitrostyrenes [J].

He, Qun ;

Xie, Fang ;

Fu, Guanghong ;

Quan, Mao ;

Shen, Chaoren ;

Yang, Guoqiang ;

Gridnev, Ilya D. ;

Zhang, Wanbin .

ORGANIC LETTERS, 2015, 17 (09) :2250-2253

[38] Asymmetric 1,4-Addition of Diarylphosphine Oxides to α, β-Unsaturated 2-Acyl Imidazoles [J].

Chen, Lirong ;

Wang, Guiyong ;

Nong, Xiufei ;

Shao, Wendi ;

Li, Jiuling ;

Guo, Yafei ;

Fan, Baomin .

CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (36)

[39] Enantio selective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes [J].

Kurihara, Kazunori ;

Sugishita, Noriyuki ;

Oshita, Kengo ;

Piao, Dongguo ;

Yamamoto, Yasunori ;

Miyaura, Norio .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (1-3) :428-435

[40] Chiral Heterodisulfoxide Ligands in Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromenones [J].

Han, Fuzhong ;

Chen, Guihua ;

Zhang, Xiangyang ;

Liao, Jian .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) :2928-2931

← 1 2 3 4 5 →