Novel chiral P,N-ferrocene ligands in palladium-catalyzed asymmetric allylic alkylations

被引：88

作者：

Zhang, WB ^{[1
]}

Yoneda, Y ^{[1
]}

Kida, T ^{[1
]}

Nakatsuji, Y ^{[1
]}

Ikeda, I ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(98)00334-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Novel chiral P,N-ferrocene ligands, 1-diphenylphosphino-1'-oxazolinylferrocenes, were prepared from ferrocene via 1,1'-bis(tributylstannyl)ferrocene and I -diphenylphosphino-1'-methoxycarbonylferrocene as intermediates, and with this new kind of ligand up to 91% ee with 99% chemical yield was afforded for the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethylmalonate anion. The complexation behavior of this kind of ligand with dichlorobis (acetonitrile)palladium and bis(mu-chloro)(1,3-diphenyl-eta(3)-allyl)dipalladium was investigated. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3371 / 3380

页数：10

共 47 条

[1] An efficient diastereoselective synthesis of chiral oxazolinylferrocene compounds [J].

Ahn, KH ;

Cho, CW ;

Baek, HH ;

Park, J ;

Lee, S .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :4937-4943

[2] Pd-Catalyzed asymmetric allylic alkylations using various diphenylphosphino(oxazolinyl)ferrocene ligands [J].

Ahn, KH ;

Cho, CW ;

Park, JW ;

Lee, SW .

TETRAHEDRON-ASYMMETRY, 1997, 8 (08) :1179-1185

[3]

AKERMARK B, 1984, ORGANOMETALLICS, V3, P679

[4] Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene [J].

Andrus, MB ;

Asgari, D ;

Sclafani, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9365-9368

[5] ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].

BALDWIN, IC ;

WILLIAMS, JMJ ;

BECKETT, RP .

TETRAHEDRON-ASYMMETRY, 1995, 6 (07) :1515-1518

[6]

Butler IR, 1996, SYNTHESIS-STUTTGART, P1350

[7] Enantioselective allylic substitution using a novel (phosphino-1,3-oxazine)palladium catalyst [J].

Evans, PA ;

Brandt, TA .

TETRAHEDRON LETTERS, 1996, 37 (51) :9143-9146

[8] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].

FROST, CG ;

HOWARTH, J ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122

[9] THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CHEMOTACTIC FACTOR SIRENIN BY AN INTRAMOLECULAR [2+1] CYCLIZATION USING A NEW CHIRAL CATALYST [J].

GANT, TG ;

NOE, MC ;

COREY, EJ .

TETRAHEDRON LETTERS, 1995, 36 (48) :8745-8748

[10] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .8. PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC AMINATION [J].

HAYASHI, T ;

YAMAMOTO, A ;

ITO, Y ;

NISHIOKA, E ;

MIURA, H ;

YANAGI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) :6301-6311

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