Asymmetric syn-Dihydroxylation of β-Substituted (2R)-N-(α,β-Enoyl)bornane-10,2-sultams†
作者： Jerzy Raczko , Michael Achmatowicz , Artur Jezewski , Christian Chapuis , Zofia Urbañczyk-Lipkowska
关键词: Crystal structure 、 Stereochemistry 、 Bornane 、 Chemical correlation 、 Chemistry 、 Side chain 、 Stereoselectivity 、 Dihydroxylation 、 Acylation
摘要: Variously β-substituted (2R)-N-[(E)-α,β-enoyl]bornane-10,2-sultams were oxidized with OsO4/4-methylmorpholine 4-oxide in a highly stereoselective manner. In all cases, the attack occurred on C(α)-re face. The absolute configurations of products determined by chemical correlation. Mechanistic considerations about reactive conformation as well fully refined X-ray crystal structures dihydroxylated are discussed. New neutral conditions for sultam acylation, applicable to preparation taxol and Taxotere® C(13) side chain Cardizem® chloramphenicol precursors, also presented.
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