SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROPEROXY SULFOXIDES BY REGIOSELECTIVE PHOTOOXYGENATION (SCHENCK REACTION) OF RACEMIC VINYL SULFOXIDES

Authors
ADAM W KUMAR AS SAHAMOLLER CR
Citation
W. Adam et al., SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROPEROXY SULFOXIDES BY REGIOSELECTIVE PHOTOOXYGENATION (SCHENCK REACTION) OF RACEMIC VINYL SULFOXIDES, Synthesis, (12), 1995, pp. 1525
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
12
Year of publication
1995
Database
ISI
SICI code
0039-7881(1995):12<1525:SOASBR>2.0.ZU;2-M
Abstract
The beta-hydroperoxy vinyl sulfoxides 3 were synthesized in good to ex cellent yields by regioselective photooxygenation of racemic vinyl sul foxides 2. Moderate diastereoselectivities were observed in the ene re action of singlet oxygen (Schenck Reaction) with the E- or Z-vinyl sul foxides 2e. Titanium-catalyzed oxygen transfer reaction of these sulfo xy-functionalized racemic allylic hydroperoxides 3 resulted chemoselec tively in the corresponding sulfones 5.