Polymer-supported C2-symmetric ligands for palladium-catalyzed asymmetric allylic alkylation reactions

被引：30

作者：

Trost, BM ^{[1
]}

Pan, ZY ^{[1
]}

Zambrano, J ^{[1
]}

Kujat, C ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2002年 / 41卷 / 24期

关键词：

allylic alkylation; asymmetric synthesis; N ligands; palladium; polymer-supported catalysts;

D O I：

10.1002/anie.200290018

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The choice of scaffold and tether has a marked influence on the enantiomeric excesses obtained in Pd-catalyzed asymmetric allylic alkylations, such as the cyclization of the bisurethane 1 to the oxazolidin-2-one 2 [Eq. (1); Ts=p-toluenesulfonate], performed with polymer-supported chiral catalysts. The best results were obtained by using an ArgoGel resin, an amide tether, and a pyrrolidine scaffold.

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页码：4691 / 4693

页数：3

相关论文

共 34 条

[1] Combinatorial chemistry for ligand development in catalysis: Synthesis and catalysis screening of peptidosulfonamide tweezers on the solid phase [J].

Brouwer, AJ ;

van der Linden, HJ ;

Liskamp, RMJ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1750-1757

[2] Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Applications in palladium(II)-mediated coupling reactions [J].

Buchmeiser, MR ;

Wurst, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11101-11107

[3] Polymer-supported catalysis in synthetic organic chemistry [J].

Clapham, B ;

Reger, TS ;

Janda, KD .

TETRAHEDRON, 2001, 57 (22) :4637-4662

[4] Supported catalysts and their applications in synthetic organic chemistry [J].

de Miguel, YR ;

Brulé, E ;

Margue, RG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (23) :3085-3094

[5] Reusable polymer-supported palladium catalysts: An alternative to tetrakis(triphenylphosphine)palladium in the Suzuki cross-coupling reaction [J].

Fenger, I ;

Le Drian, C .

TETRAHEDRON LETTERS, 1998, 39 (24) :4287-4290

[6]

Fodor K, 1999, ENANTIOMER, V4, P497

[7] Polymer-bound bis(oxazoline) as a chiral catalyst [J].

Hallman, K ;

Moberg, C .

TETRAHEDRON-ASYMMETRY, 2001, 12 (10) :1475-1478

[8] Enantioselective allylic alkylation using polymer-supported palladium catalysts [J].

Hallman, K ;

Macedo, E ;

Nordström, K ;

Moberg, C .

TETRAHEDRON-ASYMMETRY, 1999, 10 (20) :4037-4046

[9] Polymer-bound palladium-catalyzed cross-coupling of organoboron compounds with organic halides and organic triflates [J].

Jang, SB .

TETRAHEDRON LETTERS, 1997, 38 (10) :1793-1796

[10] Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation [J].

Ley, SV ;

Baxendale, IR ;

Bream, RN ;

Jackson, PS ;

Leach, AG ;

Longbottom, DA ;

Nesi, M ;

Scott, JS ;

Storer, RI ;

Taylor, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (23) :3815-4195

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