SYNTHESIS OF CHIRAL URETHANE N-ALKOXYCARBONYL TETRAMIC ACIDS FROM URETHANE N-CARBOXYANHYDRIDES (UNCAS)

Authors
FEHRENTZ JA BOURDEL E CALIFANO JC CHALOIN O DEVIN C GARROUSTE P LIMALEITE AC LLINARES M RIEUNIER F VIZAVONNA J WINTERNITZ F LOFFET A MARTINEZ J
Citation
Ja. Fehrentz et al., SYNTHESIS OF CHIRAL URETHANE N-ALKOXYCARBONYL TETRAMIC ACIDS FROM URETHANE N-CARBOXYANHYDRIDES (UNCAS), Tetrahedron letters, 35(10), 1994, pp. 1557-1560
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
10
Year of publication
1994
Pages
1557 - 1560
Database
ISI
SICI code
0040-4039(1994)35:10<1557:SOCUNT>2.0.ZU;2-U
Abstract
The synthesis of chiral N-protected tetramic acid derivatives which ar e important precursors of beta-hydroxy gamma-amino acid under mild con ditions is described. Reaction of urethane-N-carboxyanhydrides (UNCAs) with Meldrum's acid in the presence of a tertiary amine, followed by subsequent cyclisation produced tetramic acid derivatives. This proced ure is applicable to Boc-, Fmoc- and Z- N-carboxyanhydrides.