Steric and chelate ring size effects on the enantioselectivity in palladium-catalyzed allylic alkylation with new chiral P,N-ligands

被引：32
|
作者：
Arena, CG [1 ]
Drommi, D [1 ]
Faraone, F [1 ]
机构：
[1] Univ Messina, Dipartimento Chim Inorgan Chim Analit & Chim Fis, I-98166 Messina, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 23期
关键词：
D O I：
10.1016/S0957-4166(00)00448-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
New chiral P,N-ligands derived from substituted pyridine and (S)-2,2'-binaphthol phosphorochloridite have been prepared and tested in asymmetric palladium-catalyzed allylic alkylations. The enantioselectivity was poorly dependent on the pyridine substituent, instead, a chelate ring size effect was apparent. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4753 / 4759
页数：7
相关论文
共 50 条
  • [41] Polymer-supported heterogeneous chiral ligands for palladium-catalyzed asymmetric allylic alkylation
    Kim, Sang-Han
    Kim, Geon-Joong
    JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2006, 12 (04) : 643 - 647
  • [42] Novel chiral phosphine-oxazinane ligands in palladium-catalyzed asymmetric allylic alkylation
    Mino, T
    Hata, S
    Ohtaka, K
    Sakamoto, M
    Fujita, T
    TETRAHEDRON LETTERS, 2001, 42 (29) : 4837 - 4839
  • [43] New dihydroxy bis(oxazoline) ligands for the palladium-catalyzed asymmetric allylic alkylation:: Experimental investigations of the origin of the reversal of the enantioselectivity
    Aït-Haddou, H
    Hoarau, O
    Cramailére, D
    Pezet, F
    Daran, JC
    Balavoine, GGA
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (03) : 699 - 707
  • [44] New chiral phosphinooxazolidine ligands for palladium-catalyzed asymmetric allylic substitution
    Jin, MJ
    Jung, JA
    Kim, SH
    TETRAHEDRON LETTERS, 1999, 40 (28) : 5197 - 5198
  • [45] Novel chiral P,N-ferrocene ligands in palladium-catalyzed asymmetric allylic alkylations
    Zhang, WB
    Yoneda, Y
    Kida, T
    Nakatsuji, Y
    Ikeda, I
    TETRAHEDRON-ASYMMETRY, 1998, 9 (19) : 3371 - 3380
  • [46] Palladium-catalyzed asymmetric allylic alkylation of indoles by C-N bond axially chiral phosphine ligands
    Mino, Takashi
    Ishikawa, Miho
    Nishikawa, Kenji
    Wakui, Kazuya
    Sakamoto, Masami
    TETRAHEDRON-ASYMMETRY, 2013, 24 (08) : 499 - 504
  • [47] New multidendate phosphine ligands and their application in palladium-catalyzed asymmetric allylic alkylation
    Pei, Yuxin
    Brule, Emilie
    Moberg, Christina
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3420 - U3421
  • [48] Synthesis and application of new iminopyridine ligands in the enantioselective palladium-catalyzed allylic alkylation
    Solinas, Maurizio
    Sechi, Barbara
    Chelucci, Giorgio
    Baldino, Salvatore
    Pedro, Jose R.
    Blay, Gonzalo
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 385 : 73 - 77
  • [49] TRANSFER OF ASYMMETRY BY THE PALLADIUM-CATALYZED ALKYLATION OF CHIRAL ALLYLIC SULFINATES
    HIROI, K
    KITAYAMA, R
    SATO, S
    CHEMISTRY LETTERS, 1984, (06) : 929 - 932
  • [50] Influence of steric symmetry and electronic dissymmetry on the enantioselectivity in palladium-catalyzed allylic substitutions
    Vasse, JL
    Stranne, R
    Zalubovskis, R
    Gayet, C
    Moberg, C
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08): : 3258 - 3270
12345