Catalytic Enantioselective Meerwein-Eschenmoser Claisen Rearrangement: Asymmetric Synthesis of Allyl Oxindoles

被引：149

作者：

Linton, Elizabeth C. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 48期

关键词：

D O I：

10.1021/ja807026z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved, Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee.

引用

页码：16162 / +

页数：3

共 33 条

[1] The catalytic diastereo- and enantioselective Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ether [J].

Abraham, L ;

Körner, M ;

Schwab, P ;

Hiersemann, M .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (11) :1281-1294

[2] Highly enantioselective catalytic asymmetric Claisen rearrangement of 2-alkoxycarbonyl-substituted allyl vinyl ethers [J].

Abraham, L ;

Körner, M ;

Hiersemann, M .

TETRAHEDRON LETTERS, 2004, 45 (18) :3647-3650

[3]

Abraham L, 2001, ANGEW CHEM INT EDIT, V40, P4700, DOI 10.1002/1521-3773(20011217)40:24<4700::AID-ANIE4700>3.0.CO

[4]

2-6

[5] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS [J].

ALLEN, JV ;

DAWSON, GJ ;

FROST, CG ;

WILLIAMS, JMJ ;

COOTE, SJ .

TETRAHEDRON, 1994, 50 (03) :799-808

[6] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory studies of intramolecular Heck reactions of (Z)-α,β-unsaturated anilides and mechanistic investigations of asymmetric Heck reactions proceeding via neutral intermediates [J].

Ashimori, A ;

Bachand, B ;

Calter, MA ;

Govek, SP ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6488-6499

[7] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].

Ashimori, A ;

Bachand, B ;

Overman, LE ;

Poon, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487

[8] A new Claisen sequence for the synthesis of 3-substituted-2-oxindoles [J].

Booker-Milburn, KI ;

Fedouloff, M ;

Paknoham, SJ ;

Strachan, JB ;

Melville, JL ;

Voyle, M .

TETRAHEDRON LETTERS, 2000, 41 (23) :4657-4661

[9] Claisen rearrangement over the past nine decades [J].

Castro, AMM .

CHEMICAL REVIEWS, 2004, 104 (06) :2939-3002

[10] Structure-based design of potent non-peptide MDM2 inhibitors [J].

Ding, K ;

Lu, Y ;

Nikolovska-Coleska, Z ;

Qiu, S ;

Ding, YS ;

Gao, W ;

Stuckey, J ;

Krajewski, K ;

Roller, PP ;

Tomita, Y ;

Parrish, DA ;

Deschamps, JR ;

Wang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10130-10131

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