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

被引：65
|
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
收藏
页码：11101 / 11103
页数：3
相关论文
共 50 条
  • [1] Palladium-catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Carboxylic Esters
    Du, Dan
    Lin, Zi-Qi
    Lu, Jun-Zhu
    Li, Chun
    Duan, Wei-Liang
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (05) : 392 - 394
  • [2] Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated Aldehydes
    Chen, Yun-Rong
    Duan, Wei-Liang
    ORGANIC LETTERS, 2011, 13 (21) : 5824 - 5826
  • [3] Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonamides
    Dai, Guo-Fa
    Song, Yu-Chuan
    Xiao, Fanhua
    Duan, Wei-Liang
    SYNTHESIS-STUTTGART, 2018, 50 (17): : 3506 - 3512
  • [4] NHC-copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones
    Chen, Yun-Rong
    Feng, Jian-Jun
    Duan, Wei-Liang
    TETRAHEDRON LETTERS, 2014, 55 (03) : 595 - 597
  • [5] Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Quinone Monoketals
    Sun, Guijiu
    Xiao, Fanhua
    Duan, Weiliang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (01) : 61 - 68
  • [6] Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonyl Fluorides
    Cheng, An-Qi
    Wu, Zeng-Hua
    Yang, Huai-Lan
    Duan, Wei-Liang
    SYNTHESIS-STUTTGART, 2023, 55 (17): : 2773 - 2778
  • [7] Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Nitroalkenes for the Synthesis of Chiral P,N-Compounds
    Feng, Jian-Jun
    Huang, Miao
    Lin, Zi-Qi
    Duan, Wei-Liang
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 3122 - 3126
  • [8] Palladium-catalyzed asymmetric addition of diarylphosphines to N-tosylimines
    Huang, Miao
    Li, Chun
    Huang, Jian
    Duan, Wei-Liang
    Xu, Sheng
    CHEMICAL COMMUNICATIONS, 2012, 48 (90) : 11148 - 11150
  • [9] Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to Enones toward the Synthesis of Chiral Phosphines
    Feng, Jian-Jun
    Chen, Xue-Feng
    Shi, Min
    Duan, Wei-Liang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) : 5562 - +
  • [10] Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds
    Lu, Junzhu
    Ye, Jinxing
    Duan, Wei-Liang
    ORGANIC LETTERS, 2013, 15 (19) : 5016 - 5019
12345