Recent Advances in the Asymmetric Conjugate Addition Reactions of Phosphorus Nucleophiles to Electron-Deficient Alkenes

被引:32
作者
Li, Zhen [1 ]
Duan, Weiliang [2 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric addition; phosphorus nucleophiles; chiral phosphorus compounds; electron-deficient alkenes; ALPHA; BETA-UNSATURATED N-ACYLPYRROLES; PALLADIUM-CATALYZED 1,4-ADDITION; PCN PINCER PALLADIUM(II); DIALKYL PHOSPHINE OXIDES; ENANTIOSELECTIVE HYDROPHOSPHINATION; MICHAEL ADDITION; ACTIVATED OLEFINS; SULFONIC ESTERS; P-C; DIARYLPHOSPHINES;
D O I
10.6023/cjoc201602018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral phosphines are very useful in the fields of asymmetric catalysis, pharmaceutical chemistry, and materials. These compounds have been used as ligands coordinated to transition metals or organocatalysts in various reactions to furnish optically active products with high efficiency. Asymmetric phosphorus-addition reaction can be utilized for the direct preparation of chiral phosphorus compounds. This review summarizes the recent progress in the field of enantioselective phosphorus-addition reactions. Several examples of transition metal- and organocatalyst-promoted asymmetric hydrophosphination reactions of electron-deficient alkenes have been introduced.
引用
收藏
页码:1805 / 1813
页数:9
相关论文
共 74 条
  • [1] Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
  • [2] 2-6
  • [3] Bansal RK, 2010, TOP HETEROCYCL CHEM, V21, P1, DOI 10.1007/978-3-642-12254-5
  • [4] Organocatalytic asymmetric hydrophosphination of nitroalkenes
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Locatelli, Manuela
    Mazzanti, Andrea
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. CHEMICAL COMMUNICATIONS, 2007, (07) : 722 - 724
  • [5] Organocatalytic Asymmetric 1,6-Addition Reactions
    Biju, Akkattu T.
    [J]. CHEMCATCHEM, 2011, 3 (12) : 1847 - 1849
  • [6] Borner A., 2008, PHOSPHORUS LIGANDS A, V1-3
  • [7] Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes
    Carlone, Armando
    Bartoli, Giuseppe
    Bosco, Marcella
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) : 4504 - 4506
  • [8] NHC-copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones
    Chen, Yun-Rong
    Feng, Jian-Jun
    Duan, Wei-Liang
    [J]. TETRAHEDRON LETTERS, 2014, 55 (03) : 595 - 597
  • [9] Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated Aldehydes
    Chen, Yun-Rong
    Duan, Wei-Liang
    [J]. ORGANIC LETTERS, 2011, 13 (21) : 5824 - 5826
  • [10] An Approach to the Efficient Syntheses of Chiral Phosphino-Carboxylic Acid Esters
    Chew, Renta Jonathan
    Sepp, Kristel
    Li, Bin-Bin
    Li, Yongxin
    Zhu, Peng-Cheng
    Tan, Nguan Soon
    Leung, Pak-Hing
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) : 3297 - 3302