Helvetica chimica acta

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

W Oppolzer, JP Barras

文献索引：Oppolzer, Wolfgang; Barras, Jean-Pierre Helvetica Chimica Acta, 1987 ,  vol. 70, p. 1666 - 1675

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被引用次数: 62

摘要

Abstract Pure (E)-or (Z)-enoylsultams 2 were Oxidized with OsO 4/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% de 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.