Asymmetric Dihydroxylations of β-Substituted N-(α,β-Enolyl)bornane-10,2-sultams

Article abstract of DOI:10.1002/hlca.19870700703

Pure (E)- or (Z)-enoylsultams 2 were oxidized with OsO4/N-methylmorpholine N-oxide in a stereospecific and highly ?-face selective manner.Acetalization of the resulting 1,2-diols furnished, after purification, the stable, crystalline acetals 6 in >99percent d.e. and in 63-74percent overall yield from 2.Reductive or hydrolytic cleavage of 6 gave enantiometrically pure alcohols 8 or carboxylic acids 9 with recovery of the sultam auxiliary 1.