New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions

被引：87

作者：

Hiroi, K ^{[1
]}

Suzuki, Y ^{[1
]}

Abe, I ^{[1
]}

Kawagishi, R ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Dept Synthet Organ Chem, Aoba Ku, Sendai, Miyagi 9818553, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 27期

关键词：

asymmetric induction; catalysis; palladium and compounds; sulfoxides;

D O I：

10.1016/S0040-4020(00)00393-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality as an alternative coordinating element were developed, and their usefulness was demonstrated by applying them to palladium-catalyzed asymmetric allylic nucleophilic substitution reactions. The structure of the catalyst precursor coordinated by the chiral phosphino sulfoxide was determined by X-ray crystallographic analysis. The possible mechanism for the asymmetric induction using these chiral ligands was proposed on the basis of the stereochemical outcome obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4701 / 4710

页数：10

共 46 条

[1]

AKERMARK B, 1984, ORGANOMETALLICS, V3, P679

[2] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].

ALLEN, JV ;

COOTE, SJ ;

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072

[3] ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION - ELECTRONIC AND STERIC EFFECTS OF THE LIGAND [J].

ALLEN, JV ;

BOWER, JF ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1895-1898

[4] OPTICALLY ACTIVE SULFOXIDES . SYNTHESIS + ROTATORY DISPERSION OF SOME DIARYL SULFOXIDES [J].

ANDERSEN, KK ;

FOLEY, JW ;

GAFFIELD, W ;

PAPANIKOLAU, NE ;

PERKINS, RI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) :5637-+

[5] Sulfur-imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation [J].

Anderson, JC ;

James, DS ;

Mathias, JP .

TETRAHEDRON-ASYMMETRY, 1998, 9 (05) :753-756

[6]

[Anonymous], CATALYTIC ASYMMETRIC

[7] SYNTHETIC APPLICATIONS OF ENANTIOSELECTIVE ORGANOTRANSITION-METAL-MEDIATED REACTIONS [J].

BLYSTONE, SL .

CHEMICAL REVIEWS, 1989, 89 (08) :1663-1679

[8] Optically active sulfoximines in enantioselective palladium catalysis [J].

Bolm, C ;

Kaufmann, D ;

Zehnder, M ;

Neuburger, M .

TETRAHEDRON LETTERS, 1996, 37 (23) :3985-3988

[9] MECHANISTIC AND SYNTHETIC STUDIES IN CATALYTIC ALLYLIC ALKYLATION WITH PALLADIUM COMPLEXES OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE [J].

BROWN, JM ;

HULMES, DI ;

GUIRY, PJ .

TETRAHEDRON, 1994, 50 (15) :4493-4506

[10]

BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645

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