Asymmetric Dihydroxylations of β-Substituted N-(α,β-Enoyl)bornane-10,2-sultams |
| |
Authors: | Wolfgang Oppolzer Jean-Pierre Barras |
| |
Abstract: | 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 auxiliary 1 . |
| |
Keywords: | |
|
|