Novel chiral sulfur-containing ferrocenyl ligands for palladium-catalyzed asymmetric allylic substitution

被引：32

作者：

Nakamura, S ^{[1
]}

Fukuzumi, T ^{[1
]}

Toru, T ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

CHIRALITY | 2004年 / 16卷 / 01期

关键词：

allylic substitution; ferrocene; enantioselective reaction; sulfoxide; P; S-bidentate ligands;

D O I：

10.1002/chir.10300

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

New chiral ferrocenyl ligands having chiral sulfinyl and phosphinyl groups were prepared. The palladium-catalyzed allylic substitution reaction using these chiral ligands showed good enantioselectivity. The mechanism for the asymmetric reaction is proposed on the basis of the stereochemical outcome. (C) 2003 Wiley-Liss, Inc.

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页码：10 / 12

页数：3

相关论文

共 34 条

[1] A new P,S-Chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand [J].

Albinati, A ;

Pregosin, PS ;

Wick, K .

ORGANOMETALLICS, 1996, 15 (10) :2419-2421

[2] CATALYTIC ACTIVITY OF CHIRAL BETA-HYDROXYSULFOXIDES IN THE ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE [J].

CARRENO, MC ;

RUANO, JLG ;

MAESTRO, MC ;

CABREJAS, LMM .

TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :727-734

[3] Chiral sulfoxides and sulfides tethered to pyridines as ligands for enantioselective catalysis: Palladium catalyzed allylic substitution and addition of diethylzinc to benzaldehyde [J].

Chelucci, G ;

Berta, D ;

Saba, A .

TETRAHEDRON, 1997, 53 (10) :3843-3848

[4] Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalysed allylic substitution [J].

Chesney, A ;

Bryce, MR ;

Chubb, RWJ ;

Batsanov, AS ;

Howard, JAK .

TETRAHEDRON-ASYMMETRY, 1997, 8 (14) :2337-2346

[5]

Enders D, 2000, EUR J ORG CHEM, V2000, P3399

[6] Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions [J].

Evans, DA ;

Campos, KR ;

Tedrow, JS ;

Michael, FE ;

Gagné, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7905-7920

[7] Chiral β-phosphino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions [J].

Hiroi, K ;

Suzuki, Y ;

Kawagishi, R .

TETRAHEDRON LETTERS, 1999, 40 (04) :715-718

[8]

Hiroi K, 1999, CHEM LETT, P149

[9] New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions [J].

Hiroi, K ;

Suzuki, Y ;

Abe, I ;

Kawagishi, R .

TETRAHEDRON, 2000, 56 (27) :4701-4710

[10] New chiral sulfoxide ligands in catalytic asymmetric Diels-Alder reactions: double acceleration by the chiralities of the sulfoxides and oxazolines [J].

Hiroi, K ;

Watanabe, K ;

Abe, I ;

Koseki, M .

TETRAHEDRON LETTERS, 2001, 42 (43) :7617-7619

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