Enantioselective Heck reactions using chiral P,N-ligands

被引:131
|
作者
Loiseleur, O [1 ]
Hayashi, M [1 ]
Keenan, M [1 ]
Schmees, N [1 ]
Pfaltz, A [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
asymmetric catalysis; oxazolines; palladium; P; N-ligands;
D O I
10.1016/S0022-328X(98)01049-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Palladium complexes with chiral phosphinooxazoline ligands are efficient catalysts far enantioselective Heck reactions with aryl or alkenyl triflates and cyclic olefins. In the arylation and alkenylation of 1,2-dihydrofuran, cyclopentene, 2,3-dihydro-4H-pyran, 4,7-dihydro-1,3-dioxepin, and N-methoxycarbonyl-2,3-dihydropyrrole high yields and good to excellent enantioselectivities have been obtained. In contrast to palladium-BINAP catalysts, the catalysts derived from phosphinooxazolines show a very low tendency to promote isomerization of the product by C-C double bond migration. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:16 / 22
页数:7
相关论文
共 50 条
  • [1] Chiral P,N-ligands based on ketopinic acid in the asymmetric heck reaction
    Gilbertson, SR
    Fu, Z
    ORGANIC LETTERS, 2001, 3 (02) : 161 - 164
  • [2] Chiral P,N-ligands for the highly enantioselective addition of diethylzinc to aromatic aldehydes
    Wang, Qiang
    Li, Shuang
    Hou, Chuan-Jin
    Chu, Ting-Ting
    Hu, Xiang-Ping
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (10)
  • [3] Synthesis of new chiral benzylically substituted P,N-ligands and their applications in the asymmetric Heck reaction
    Hou, XL
    Dong, DX
    Yuan, K
    TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2189 - 2191
  • [4] Enantioselective Synthesis of Isoindolones via Palladium - Catalyzed Intramolecular Heck-Mizoroki Reactions of Endocyclic Enamides Using N,N-Ligands
    Wiethan, Carson
    Braga, Ingredy B.
    Menezes da Silva, Vitor H.
    Batista Jr, Joao M.
    Correia, Carlos Roque D.
    CHEMCATCHEM, 2023, 15 (12)
  • [5] Chiral P,N,N-Ligands for Asymmetric Hydrogenation
    Liang, Ding-Hua
    Hou, Chuan-Jin
    Li, Qi
    Qin, Hao
    Li, Ling
    Hu, Xiang-Ping
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2165 - 2185
  • [6] Synthesis of camphor-based chiral P,N-ligands
    Ilaldinov, I. Z.
    Fatkulina, D. A.
    Kadyrov, R.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (06) : 952 - 953
  • [7] Enantioselective Baeyer-Villiger oxidation catalyzed by palladium(II) complexes with chiral P,N-ligands
    Malkov, Andrei V.
    Friscourt, Frederic
    Bell, Mark
    Swarbrick, Martin E.
    Kocovsky, Pavel
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11): : 3996 - 4003
  • [8] Palladium-catalyzed asymmetric allylic alkylation using chiral P,N-ligands
    Mino, T
    Tanaka, Y
    Sakamoto, M
    Fujita, T
    HETEROCYCLES, 2000, 53 (07) : 1485 - 1488
  • [9] Enantioselective catalyses;: 126:: Axially chiral N,N-ligands with binaphthyl/bipyridyl structure
    Brunner, H
    Olschewski, G
    Nuber, B
    SYNTHESIS-STUTTGART, 1999, (03): : 429 - 434
  • [10] The synthesis of new chiral P,N-ligands on the basis of camphor
    Ilaldinov, Ilyas
    Fatkulina, Daniya
    Bucharov, Sergey
    Jackstell, Ralf
    Spannenberg, Anke
    Beller, Matthias
    Kadyrov, Renat
    TETRAHEDRON-ASYMMETRY, 2011, 22 (20-22) : 1936 - 1941