Reaction of sugar allyltins with aldehydes. A remarkable difference in reactivity between furanose and pyranose organometallic derivatives

Authors
Jarosz, S Skora, S Szewczyk, K Ciunik, Z
Citation
S. Jarosz et al., Reaction of sugar allyltins with aldehydes. A remarkable difference in reactivity between furanose and pyranose organometallic derivatives, TETRAHEDR-A, 12(13), 2001, pp. 1895-1905
Citations number
39
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
13
Year of publication
2001
Pages
1895 - 1905
Database
ISI
SICI code
0957-4166(20010730)12:13<1895:ROSAWA>2.0.ZU;2-0
Abstract
The reaction of organometallic derivatives of monosaccharides with aldehyde s catalyzed with BF3. OEt2 was studied. A significant difference in reactiv ity between the pyranosidic and furanosidic allyltins was noted. The former reacted readily with aldehydes affording precursors of higher carbon sugar s with very high stereoselectivity, while the latter underwent rearrangemen t with elimination of the stannyl moiety prior to reaction with the aldehyd e. (C) 2001 Elsevier Science Ltd. All rights reserved.