P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation

被引:15
|
作者
Xiong, Wenrui [1 ]
Xu, Guangqing [2 ]
Yu, Xinhong [1 ]
Tang, Wenjun [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, 130 Meilong Rd, Shanghai 200037, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
SUBSTITUTION-REACTION; ENANTIOSELECTIVE ALLYLATION; CONJUGATE ADDITION; CLOSING METATHESIS; GRIGNARD-REAGENTS; HYDROXYALKYL NHC; EFFICIENT; PHOSPHATES; S(N)2'; CHLORIDES;
D O I
10.1021/acs.organomet.9b00194
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Asymmetric copper-catalyzed allylic alkylation between allylic bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.
引用
收藏
页码:4003 / 4013
页数:11
相关论文
共 50 条
  • [31] New modular P-chiral ligands for Rh-catalyzed asymmetric hydrogenation
    Bondarev, Oleg G.
    Goddard, Richard
    TETRAHEDRON LETTERS, 2006, 47 (51) : 9013 - 9015
  • [32] Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds
    Guduguntla, Sureshbabu
    Hornillos, Valentin
    Tessier, Romain
    Fananas-Mastral, Martin
    Feringa, Ben L.
    ORGANIC LETTERS, 2016, 18 (02) : 252 - 255
  • [33] Chiral phosphinooxazolines as ligands in asymmetric catalysis: Intramolecular Pd-catalyzed allylic alkylation
    Koch, G
    Pfaltz, A
    TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2213 - 2216
  • [34] Chiral Phosphaalkene-Oxazoline Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation
    Dugal-Tessier, Julien
    Dake, Gregory R.
    Gates, Derek P.
    ORGANIC LETTERS, 2010, 12 (20) : 4667 - 4669
  • [35] New enantioselective chiral imidazolidine ligands for Pd-catalyzed asymmetric allylic alkylation
    Lee, EK
    Kim, SH
    Jung, BH
    Ahn, WS
    Kim, GJ
    TETRAHEDRON LETTERS, 2003, 44 (09) : 1971 - 1974
  • [36] Novel and efficient chiral sulfideoxathiane ligands for palladium-catalyzed asymmetric allylic alkylation
    Okuyama, Y
    Nakano, H
    Takahashi, K
    Hongo, H
    Kabuto, C
    CHEMICAL COMMUNICATIONS, 2003, (04) : 524 - 525
  • [37] Enantioselective copper-catalyzed allylic alkylation with diorganozinc compounds using phosphoramidite ligands.
    Arnold, LA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : B186 - B187
  • [38] P-Chiral monodentate diamidophosphites as ligands for Rh-catalyzed asymmetric reactions
    Lyubimov, S. E.
    Davankov, V. A.
    Petrovskii, P. V.
    Loim, N. M.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (10) : 2094 - 2096
  • [39] Copper-Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Allyl Bromides with Organolithium Compounds
    Li, Jun
    Song, Xiao
    Wu, Fusong
    You, Hengzhi
    Chen, Fen-Er
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (34)
  • [40] Mechanistic identification and improvement of a direct enantioconvergent transformation in copper-catalyzed asymmetric allylic alkylation
    Langlois, Jean-Baptiste
    Emery, Daniel
    Mareda, Jiri
    Alexakis, Alexandre
    CHEMICAL SCIENCE, 2012, 3 (04) : 1062 - 1069