130. Asymmetric Dihydroxylations of β-Substituted N-(α,β-Enoyl)bornane-10,2-sultams
     Oppolzer, W.; Barras, J.-P.
     Helv. Chim. Acta 1987, 70, 1666-1675

Pure (E)- or (Z)-enoylsultams 2 were Oxidized with OsO₄/N-Methylmorpholine N-oxide in a stereospecific and highly π-face-selective manner. Acetalization of the resulting 1,2-diols furnished, after purification, the stable, crystalline acetals 6 in >99% d.e. and in 63–74% overall yield from 2. Reductive or hydrolytic cleavage of 6 gave enantiomerically pure alcohols 8 or carboxylic acids 9 with recovery of the sultan auxiliary1.

DOI : 10.1002/hlca.19870700703 

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