Enantioselective syntheses of orthogonally protected tricarballylic acid esters

Authors
Harmat, NJS Mangani, S Perrotta, E Giannotti, D Nannicini, R Altamura, M
Citation
Njs. Harmat et al., Enantioselective syntheses of orthogonally protected tricarballylic acid esters, TETRAHEDR L, 41(8), 2000, pp. 1261-1264
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
8
Year of publication
2000
Pages
1261 - 1264
Database
ISI
SICI code
0040-4039(20000219)41:8<1261:ESOOPT>2.0.ZU;2-6
Abstract
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 der ived from chiral but-3-enoyloxazolidinone imides (3) with tert-butyl bromoa cetate; following the hydrolysis to remove the chiral auxiliary, benzyl est erification afforded the 2-allyl succinic acid diesters (4) that were conve rted to protected TCA esters after oxidation of the double bond. (C) 2000 E lsevier Science Ltd. All rights reserved.