Stereoselection in radical cyclization of beta-alkoxyvinyl sulfoxides: synthesis of tetrahydrofuranyl allyl carbinols.
[reaction: see text] Tetrahydrofuranyl allyl carbinols may be prepared stereoselectively via radical cyclization of beta-alkoxyvinyl sulfoxides, Pummerer rearrangement, and reaction with allylstannane.
Keum
Gyochang
G
School of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-747, Korea.
Kang
Soon Bang
SB
Kim
Youseung
Y
Lee
Eun
E
D000498:Allyl Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis*; D000432:Methanol / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000498:Allyl Compounds; D005609:Free Radicals; D005663:Furans; D013454:Sulfoxides; D014753:Vinyl Compounds; D000432:Methanol