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

页码：1769 / 1772

页数：4

共 21 条

[1] SYNTHETIC APPLICATIONS OF ENANTIOSELECTIVE ORGANOTRANSITION-METAL-MEDIATED REACTIONS
BLYSTONE, SL
[J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1663 - 1679
[2] BIS(4,5-DIHYDROOXAZOLYL) DERIVATIVES IN ASYMMETRIC CATALYSIS
BOLM, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05): : 542 - 543
[3] Bolm C., 1991, ANGEW CHEM, V103, P556
[4] BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645
[5] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES
CONSIGLIO, G
WAYMOUTH, RM
[J]. CHEMICAL REVIEWS, 1989, 89 (01) : 257 - 276
[6] ASYMMETRIC-SYNTHESIS OF (+)-2,2,3-TRIMETHYLHEX-4-ENAL VIA NUCLEOPHILIC-ATTACK ON ETA-3-1,3-DIMETHYLALLYL COMPLEXES OF MOLYBDENUM
FALLER, JW
CHAO, KH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) : 3893 - 3898
[7] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION
FROST, CG
HOWARTH, J
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1089 - 1122
[8] MODIFICATION OF OPTICALLY-ACTIVE FERROCENYLPHOSPHINE LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC ALKYLATION
HAYASHI, T
YAMAMOTO, A
HAGIHARA, T
ITO, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (02) : 191 - 194
[9] Hayashi T., 1985, ASYMMETRIC SYNTHESIS, V5, P147
[10] HELMCHEN G, 1991, SYNLETT, P257

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