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

Article Article scientifique Article Asymmetric Dihydroxylations of β-Substituted N-(α,β-Enoyl)bornane-10,2-sultams eng 2004-10-25 1987-11-04 author Von Oppolzer Wolfgang 25270 author Barras Jean-Pierre 31402 1666-1675 10.1002/hlca.19870700703 0018-019X https://onlinelibrary.wiley.com/doi/10.1002/hlca.19870700703 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. Dewey 540 36 Département de chimie organique 141 false Helvetica chimica acta 70 7 b9a4dbb0-5c40-4c83-85d6-e97ab5b74270 Article (Published version) Restricted hlca.19870700703.pdf 677722 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Asymmetric Dihydroxylations of β-Substituted N-(α,β-Enoyl)bornane-10,2-sultams	Helvetica chimica acta			1987	161	0

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Barras, Jean-Pierre