Synthesis and application of novel chiral phosphino-oxazoline ligands with 1,1′-binaphthyl skeleton

被引：112

作者：

Ogasawara, M ^{[1
]}

Yoshida, K ^{[1
]}

Kamei, H ^{[1
]}

Kato, K ^{[1
]}

Uozumi, Y ^{[1
]}

Hayashi, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 10期

基金：

日本学术振兴会;

关键词：

D O I：

10.1016/S0957-4166(98)00136-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

C-1-Symmetric phosphino-oxazolines, (S,S)- and (S,R)-2-[4-(isopropyl)oxazol-2-yl]-2'-diphenylphosphino-1,1'-binaphthyl, which possess both phosphine and oxazoline moieties, were prepared from racemic binaphthol and enantiomerically pure (S)-(+)-2-amino-3-methyl-1-butanol in high yields. Reaction of 1,3-diphenyl-2-propenyl acetate with dimethyl sodiomalonate in the presence of 2 mol% of palladium catalysts bearing the new chiral ligands proceeded with high enantioselectivity to give allylic alkylation products of up to 91% ee. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：1779 / 1787

页数：9

共 38 条

[1] BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645
[2] ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES
CONSIGLIO, G
WAYMOUTH, RM
[J]. CHEMICAL REVIEWS, 1989, 89 (01) : 257 - 276
[3] DANT TP, 1971, J CHEM SOC CHEM COMM, P481
[4] ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (19) : 3149 - 3150
[5] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION
FROST, CG
HOWARTH, J
WILLIAMS, JMJ
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (09) : 1089 - 1122
[6] CHIRAL ORGANOLANTHANIDES DESIGNED FOR ASYMMETRIC CATALYSIS - SYNTHESIS, CHARACTERIZATION, AND CONFIGURATIONAL INTERCONVERSIONS OF CHIRAL, C-1-SYMMETRICAL ORGANOLANTHANIDE HALIDES, AMIDES, AND HYDROCARBYLS
GIARDELLO, MA
CONTICELLO, VP
BRARD, L
SABAT, M
RHEINGOLD, AL
STERN, CL
MARKS, TJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) : 10212 - 10240
[7] MOP - A MONODENTATE CHIRAL PHOSPHINE LIGAND FOR CATALYTIC ASYMMETRIC REACTIONS
HAYASHI, T
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (11) : 900 - 911
[8] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION
HAYASHI, T
YAMAMOTO, A
ITO, Y
NISHIOKA, E
MIURA, H
YANAGI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6301 - 6311
[9] 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
[10] CATALYTIC ASYMMETRIC REDUCTION OF ALLYLIC ESTERS WITH FORMIC-ACID CATALYZED BY PALLADIUM MOP COMPLEXES
HAYASHI, T
IWAMURA, H
NAITO, M
MATSUMOTO, Y
UOZUMI, Y
MIKI, M
YANAGI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) : 775 - 776

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