PHOSPHINOARYLOXAZOLINES AND PHOSPHINOALKYLOXAZOLINES AS NEW CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS - VERY HIGH ENANTIOSELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTIONS

被引：592
|
作者：
SPRINZ, J [1 ]
HELMCHEN, G [1 ]
机构：
[1] UNIV HEIDELBERG,INST ORGAN CHEM,IM NEUENHEIMER FELD 270,W-6900 HEIDELBERG,GERMANY
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 11期
关键词：
D O I：
10.1016/S0040-4039(00)60774-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral phosphinoaryl- and phosphinoalkyloxazolines, a new class of chelate ligands, were prepared via convenient routes. Palladium complexes of the new ligands have proved to be highly effective catalysts for allylic substitution reactions. Enantioselectivity of up to 98.5 % ee in the reaction of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate is the highest so far achieved in this area.
引用
收藏
页码：1769 / 1772
页数：4
相关论文
共 50 条
  • [21] ENANTIOSELECTIVE PALLADIUM CATALYZED ALLYLIC SUBSTITUTION WITH THIENYL OXAZOLINE LIGANDS
    FROST, CG
    WILLIAMS, JMJ
    TETRAHEDRON LETTERS, 1993, 34 (12) : 2015 - 2018
  • [22] New chiral N,S-ligands with thiophenyl at benzylic position palladium (II)-catalyzed enantioselective allylic alkylation
    Wu, H
    Wu, XW
    Hou, XL
    Dai, LX
    Wang, QR
    CHINESE JOURNAL OF CHEMISTRY, 2002, 20 (09) : 816 - 818
  • [23] New chiral ligands, pyridinooxathianes, for palladium-catalyzed asymmetric allylic alkylation
    Okuyama, Y
    Nakano, H
    Kabuto, C
    Nozawa, R
    Takahashi, K
    Hongo, H
    HETEROCYCLES, 2002, 58 : 457 - 469
  • [24] New chiral phosphinooxazolidine ligands for palladium-catalyzed asymmetric allylic substitution
    Jin, MJ
    Jung, JA
    Kim, SH
    TETRAHEDRON LETTERS, 1999, 40 (28) : 5197 - 5198
  • [25] 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
  • [26] 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
  • [27] Steric and chelate ring size effects on the enantioselectivity in palladium-catalyzed allylic alkylation with new chiral P,N-ligands
    Arena, CG
    Drommi, D
    Faraone, F
    TETRAHEDRON-ASYMMETRY, 2000, 11 (23) : 4753 - 4759
  • [28] Palladium-Catalyzed Enantioselective Indole Allylic Alkylation with Chiral Phosphoramidite-Selenide-Based Ligands
    Feng, Bin
    Zhang, Yun-Fan
    Li, Shan
    You, Ge-Yun
    Xuan, Jun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (02)
  • [29] Enantioselective palladium catalyzed allylic substitution using chiral P,N,O Schiff base ligands
    Kwong, HL
    Cheng, LS
    Lee, WS
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 150 (1-2) : 23 - 29
  • [30] Effective Chiral Ferrocenyl Phosphine-Thioether Ligands in Enantioselective Palladium-Catalyzed Allylic Alkylations
    Cheung, Hong Yee
    Yu, Wing-Yiu
    Au-Yeung, Terry T. L.
    Zhou, Zhongyuan
    Chan, Albert S. C.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (09) : 1412 - 1422
12345