beta-Oxy-alpha-diazo-carbonyl compounds. Part 6: Synthesis and reactivity of 3-deoxy-2-diazo-esters derived from monosaccharides. Applications in thesynthesis of 2-C-alkyl-KDO analogues and related compounds

Authors
Sarabia, F Lopez-Herrera, FJ
Citation
F. Sarabia et Fj. Lopez-herrera, beta-Oxy-alpha-diazo-carbonyl compounds. Part 6: Synthesis and reactivity of 3-deoxy-2-diazo-esters derived from monosaccharides. Applications in thesynthesis of 2-C-alkyl-KDO analogues and related compounds, TETRAHEDR L, 42(50), 2001, pp. 8805-8809
Citations number
78
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
50
Year of publication
2001
Pages
8805 - 8809
Database
ISI
SICI code
0040-4039(200112)42:50<8805:BCP6SA>2.0.ZU;2-Z
Abstract
Reactions of 6-O-protected diazo derivatives 8, 9 and 10 with transition me tals Rh(II) and Cu(II) under a variety of different conditions of solvents and temperatures, were studied in order to obtain 2-C-alkyl analogues of KD O. In fact, these types of products (11, 12) were obtained in good yields w hen Rh(II) was used as a catalyst in benzene. The interesting seven-membere d ring products (13) were obtained only for 8 and 9, as single diastereoiso mers and their formations were favored when Cu(II) catalysts were used. (C) 2001 Elsevier Science Ltd. All rights reserved.