Studies of the asymmetric [2+2] cycloaddition of silylketenes and aldehydes employing Ti-TADDOL catalysts

被引：33

作者：

Yang, HW ^{[1
]}

Romo, D ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(98)00422-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ti-TADDOL catalysts provide good reactivity and moderate enantioselectivity in the asymmetric [2+2] cycloaddition of silyl ketenes and aldehydes. The effects of potential bidentate chelation of benzyloxy substituted aldehydes and of the steric size of the ketene silyl group were studied. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：2877 / 2880

页数：4

相关论文

共 34 条

[1]

[Anonymous], COMPREHENSIVE ORGANI

[2] Highly stereocontrolled synthesis of substituted propiolactones and butyrolactones from achiral lithium enolates and homochiral aldehydes [J].

Arrastia, I ;

Lecea, B ;

Cossio, FP .

TETRAHEDRON LETTERS, 1996, 37 (02) :245-248

[3] SYNTHESIS OF THE BETA-LACTONE ESTERASE INHIBITOR VALILACTONE USING PI-ALLYLTRICARBONYLIRON LACTONE COMPLEXES [J].

BATES, RW ;

FERNANDEZMORO, R ;

LEY, SV .

TETRAHEDRON LETTERS, 1991, 32 (23) :2651-2654

[4] TRIMETHYLSILYLKETENE - CYCLOADDITIONS OF KETENES AND ALDEHYDES [J].

BRADY, WT ;

SAIDI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :733-737

[5] A PROTOCOL FOR THE EFFICIENT SYNTHESIS OF ENANTIOPURE BETA-SUBSTITUTED BETA-LACTONES [J].

CAPOZZI, G ;

ROELENS, S ;

TALAMI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7932-7936

[6]

CASEGREEN SC, 1991, SYNLETT, P779

[7] ORGANOALUMINUM-PROMOTED CYCLOADDITION OF TRIALKYLSILYLKETENE WITH ALDEHYDES - A NEW, STEREOSELECTIVE APPROACH TO CIS-2-OXETANONES AND 2(Z)-ALKENOIC ACIDS [J].

CONCEPCION, AB ;

MARUOKA, K ;

YAMAMOTO, H .

TETRAHEDRON, 1995, 51 (14) :4011-4020

[8] HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX [J].

COREY, EJ ;

ISHIHARA, K .

TETRAHEDRON LETTERS, 1992, 33 (45) :6807-6810

[9] SPECTROSCOPIC STUDIES ON THE STRUCTURE AND CONFORMATION OF LEWIS ACID ALDEHYDE COMPLEXES [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3133-3139

[10]

DIRAT O, 1995, SYNLETT, P935

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