Enantioselective syntheses of orthogonally protected tricarballylic acid esters

被引：11

作者：

Harmat, NJS ^{[1
]}

Mangani, S ^{[1
]}

Perrotta, E ^{[1
]}

Giannotti, D ^{[1
]}

Nannicini, R ^{[1
]}

Altamura, M ^{[1
]}

机构：

[1] Menarini Ric SPA, Dept Chem, I-50131 Florence, Italy

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

关键词：

alkylation; asymmetric synthesis; carboxylic acids; oxazolidinones; protecting groups;

D O I：

10.1016/S0040-4039(99)02264-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3(S) and 3(R)-Benzyloxycarbonyl-pentanedioic acid mono-tert-butyl esters (6) were obtained as enantiopure orthogonally protected tricarballylic acid (TCA) esters. These were synthesised by alkylation of the sodium enolate derived from chiral but-3-enoyloxazolidinone imides (3) with tert-butyl bromoacetate; following the hydrolysis to remove the chiral auxiliary, benzyl esterification afforded the 2-allyl succinic acid diesters (4) that were converted to protected TCA esters after oxidation of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：1261 / 1264

页数：4

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