CHLOROTRIMETHYLSILANE MEDIATED FORMATION OF OMEGA-ALLYL ESTERS OF ASPARTIC AND GLUTAMIC ACIDS

被引：34

作者：

BELSHAW, PJ

MZENGEZA, S

LAJOIE, GA

机构：

[1] Department of Chemistry, University of Waterloo, Waterloo

来源：

SYNTHETIC COMMUNICATIONS | 1990年 / 20卷 / 20期

关键词：

D O I：

10.1080/00397919008051540

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The protection of the ω-carboxylic function of aspartic and glutamic acids by an allyl ester is advantageous because of its orthogonality with most protecting groups and its compatibility with a number of reagents. In this communication we describe a simple method using chlorotrimethylsilane in the presence of allyl alcohol which gives exclusively the ω-allyl esters of both aspartic and glutamic acids in excellent yield. © 1990, Taylor & Francis Group, LLC. All rights reserved.

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页码：3157 / 3160

页数：4

相关论文

共 13 条

[1] ASYMMETRIC AMINO-ACID SYNTHESIS - PREPARATION OF THE BETA-ANION DERIVED FROM ASPARTIC-ACID [J].

BALDWIN, JE ;

MOLONEY, MG ;

NORTH, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :833-834

[2] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - SYNTHESIS OF BETA, GAMMA-UNSATURATED ALPHA-AMINO-ACIDS FROM ASPARTIC-ACID [J].

BALDWIN, JE ;

MOLONEY, MG ;

NORTH, M .

TETRAHEDRON, 1989, 45 (19) :6319-6330

[3]

BROOK MA, 1983, SYNTHESIS-STUTTGART, P201

[4] SELECTIVE CLEAVAGE OF ALLYL ETHERS UNDER MILD CONDITIONS BY TRANSITION-METAL REAGENTS [J].

COREY, EJ ;

SUGGS, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (18) :3224-3224

[5] MILD PALLADIUM (0)-CATALYZED DEPROTECTION OF ALLYL ESTERS - A USEFUL APPLICATION IN THE SYNTHESIS OF CARBAPENEMS AND OTHER BETA-LACTAM DERIVATIVES [J].

DEZIEL, R .

TETRAHEDRON LETTERS, 1987, 28 (38) :4371-4372

[6] C-C LINKAGE OF CARBOXYLIC-ACIDS WITH ALLYL ALCOHOLS USING 2-PHENYLGLYCINE AS VEHICLE [J].

ENGEL, N ;

KUBEL, B ;

STEGLICH, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (06) :394-396

[7]

GREENE TW, 1981, PROTECTIVE GROUP ORG, P169

[8] SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS [J].

KUNZ, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :294-308

[9]

KUNZ H, 1985, INT J PEPT PROT RES, V26, P493

[10] THE ALLYL GROUP AS MILDLY AND SELECTIVELY REMOVABLE CARBOXY-PROTECTING GROUP FOR THE SYNTHESIS OF LABILE O-GLYCOPEPTIDES [J].

KUNZ, H ;

WALDMANN, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :71-72