Addition of silyl ketene acetals to nitrones catalyzed by lanthanide triflates

被引：40

作者：

Qian, CT ^{[1
]}

Wang, LC ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2000年 / 56卷 / 37期

关键词：

alpha-aryl-N-phenyl nitrone; Lewis acid; lanthanine triflates;

D O I：

10.1016/S0040-4020(00)00636-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Aryl-N-phenyl nitrones reacted with silyl ketene acetals mediated by lanthanum trifloromethanesulfonate (triflate) to afford the addition product in excellent yield under mild conditions. alpha-Aryl-N-tert-butyl nitrone reacted with ethyl trimethylsilylacetate to yield the unexpected alpha,beta-unsaturated ester in a 100% E-form. A possible mechanism for the process is discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7193 / 7197

页数：5

相关论文

共 34 条

[1]

Aggarwal VK, 1998, SYNTHESIS-STUTTGART, P1822

[2] Scandium trifluoromethanesulfonate, a novel catalyst for the addition of allyltrimethylsilane to aldehydes. [J].

Aggarwal, VK ;

Vennall, GP .

TETRAHEDRON LETTERS, 1996, 37 (21) :3745-3746

[3] YTTERBIUM TRIFLUOROMETHANESULFONATE [YB(OTF)(3)] AS A NOVEL CATALYST FOR THE ALLYLATION OF ALDEHYDES [J].

ASPINALL, HC ;

BROWNING, AF ;

GREEVES, N ;

RAVENSCROFT, P .

TETRAHEDRON LETTERS, 1994, 35 (26) :4639-4640

[4] REGIOSELECTIVE ADDITION OF 1-TRIMETHYLSILYLOXY-1-METHOXY-1,3-DIENES TO ALDONITRONES CATALYZED BY TRIMETHYLSILYL TRIFLATE [J].

CAMILETTI, C ;

DHAVALE, DD ;

DONATI, F ;

TROMBINI, C .

TETRAHEDRON LETTERS, 1995, 36 (40) :7293-7296

[5] TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE-PROMOTED CYCLOADDITION OF NITRONES WITH SILYL ENOL ETHERS - SYNTHESIS AND REACTIVITY OF 5-SILOXYISOXAZOLIDINES [J].

CAMILETTI, C ;

DHAVALE, DD ;

GENTILUCCI, L ;

TROMBINI, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (24) :3157-3165

[6] LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES [J].

CHINI, M ;

CROTTI, P ;

FAVERO, L ;

MACCHIA, F ;

PINESCHI, M .

TETRAHEDRON LETTERS, 1994, 35 (03) :433-436

[7] YTTRIUM TRIFLATE-CATALYZED ADDITION OF LITHIUM ENOLATES TO 1,2-EPOXIDES - EFFICIENT SYNTHESIS OF GAMMA-HYDROXY KETONES [J].

CROTTI, P ;

DIBUSSOLO, V ;

FAVERO, L ;

MACCHIA, F ;

PINESCHI, M .

TETRAHEDRON LETTERS, 1994, 35 (35) :6537-6540

[8] TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE PROMOTED [3+2] DIPOLAR CYCLOADDITION OF NITRONES AND SILYL ENOL ETHERS - AN EFFICIENT ROUTE TO 5-SILOXYISOXAZOLIDINES [J].

DHAVALE, DD ;

TROMBINI, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1268-1270

[9]

DHAVALE DD, 1992, HETEROCYCLES, V34, P2253

[10] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde [J].

Evans, DA ;

Kozlowski, MC ;

Murry, JA ;

Burgey, CS ;

Campos, KR ;

Connell, BT ;

Staples, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :669-685

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