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
  • [1] Enantioselective palladium-catalyzed allylic substitutions with asymmetric chiral ligands
    Helmchen, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 203 - 214
  • [2] Enantioselective palladium catalyzed allylic substitution with chiral pyridine ligands
    Chelucci, G
    Caria, V
    Saba, A
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) : 51 - 55
  • [3] PALLADIUM-CATALYZED, ENANTIOSELECTIVE ALLYLIC SUBSTITUTIONS
    REISER, O
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 547 - 549
  • [4] Enantioselective palladium catalyzed allylic substitution with new chiral pyridine-phosphine ligands
    Brunel, JM
    Constantieux, T
    Labande, A
    Lubatti, F
    Buono, G
    TETRAHEDRON LETTERS, 1997, 38 (34) : 5971 - 5974
  • [5] 1-phosphino-2-sulfenylferrocenes as planar chiral ligands in enantioselective palladium-catalyzed allylic substitutions
    Mancheño, OG
    Priego, J
    Cabrera, S
    Arrayás, RG
    Llamas, T
    Carretero, JC
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09): : 3679 - 3686
  • [6] New chiral phosphine-phosphite ligands in the enantioselective palladium-catalyzed allylic alkylation
    Deerenberg, S
    Schrekker, HS
    van Strijdonck, GPF
    Kamer, PCJ
    van Leeuwen, PWNM
    Fraanje, J
    Goubitz, K
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16): : 4810 - 4817
  • [7] Enantioselective palladium catalyzed allylic amination using new chiral pyridine-phosphine ligands
    Constantieux, T
    Brunel, JM
    Labande, A
    Buono, G
    SYNLETT, 1998, (01) : 49 - +
  • [8] Novel phosphinobioxazines as chiral ligands in palladium-catalyzed enantioselective allylic substitution
    Lee, SG
    Lee, SH
    Song, CE
    Chung, BY
    TETRAHEDRON-ASYMMETRY, 1999, 10 (09) : 1795 - 1802
  • [9] Application of chiral dipyridylmethane ligands in the enantioselective palladium-catalyzed allylic alkylation
    Chelucci, G
    Chessa, S
    Orrù, G
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 220 (02) : 145 - 151
  • [10] Chiral Imidazoline-Phosphine Ligands for Palladium-Catalyzed Asymmetric Allylic Substitutions
    Mei, Liang-yong
    Yuan, Zhi-liang
    Shi, Min
    ORGANOMETALLICS, 2011, 30 (23) : 6466 - 6475
12345