Stability of regioisomeric sugar allyltins. Cleavage of the carbon-oxygen bond under radical conditions

Authors
Jarosz, S Szewczyk, K
Citation
S. Jarosz et K. Szewczyk, Stability of regioisomeric sugar allyltins. Cleavage of the carbon-oxygen bond under radical conditions, TETRAHEDR L, 42(16), 2001, pp. 3021-3024
Citations number
6
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
16
Year of publication
2001
Pages
3021 - 3024
Database
ISI
SICI code
0040-4039(20010416)42:16<3021:SORSAC>2.0.ZU;2-K
Abstract
Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at hi gh temperature (140 degreesC) with elimination of the tin moiety and openin g of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH- CO2Me to afford the corresponding trienes, which spontaneously undergo ster eoselective intramolecular [4+2] cycloaddition to optically pure, highly ox ygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH= CHCH2-SnBu3] are thermally stable and do not decompose up to 170 degreesC. (C) 2001 Elsevier Science Ltd. All rights reserved.