NEW CARBON-CARBON BOND FORMATION THROUGH OXYALLYLATION OF ENOXYSILANES WITH SULFUR-DIOXIDE ADDUCT OF 1-METHOXYBUTADIENE - STEREOSELECTIVE SYNTHESIS OF (Z)-4-METHOXY-6-OXOALK-2-ENYL METHYL SULFONES

Authors
DEGUIN B ROULET JM VOGEL P
Citation
B. Deguin et al., NEW CARBON-CARBON BOND FORMATION THROUGH OXYALLYLATION OF ENOXYSILANES WITH SULFUR-DIOXIDE ADDUCT OF 1-METHOXYBUTADIENE - STEREOSELECTIVE SYNTHESIS OF (Z)-4-METHOXY-6-OXOALK-2-ENYL METHYL SULFONES, Tetrahedron letters, 38(35), 1997, pp. 6197-6200
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
35
Year of publication
1997
Pages
6197 - 6200
Database
ISI
SICI code
0040-4039(1997)38:35<6197:NCBFTO>2.0.ZU;2-0
Abstract
Mixtures of 1-methoxybutadiene, trimethylsilyl enol ethers, SO2 and a Lewis acid catalyst generate trimethylsilyl (Z)-4-methoxy-6-oxoalk-2-e nesulfinates that can be converted into 4-methoxy-6-oxoalk-2-enyl meth yl sulfones and 5-alkyl-4-methoxy-6-oxoalk-2-enyl methyl sulfones with 100% (Z) selectivity and good syn diastereoselectivity for the 5-alky l and 4-methoxy substituents. (C) 1997 Elsevier Science Ltd.