Synthesis of Novel 3-Deoxy-3-thio Derivatives of d-Glucosamine and Their Application as Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde

新型 3-脱氧-3-硫代 d-葡萄糖胺衍生物的合成及其作为二乙基锌与苯甲醛对映选择性加成反应的配体的应用

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作者:Yusuf Zaim Hakim, Tomasz Bauer

Abstract

A series of novel thio-derivatives of d-glucosamine has been synthesized using double inversion procedures at the C3 atom. New compounds were applied as ligands for the diethylzinc addition to benzaldehyde and the products of the addition were obtained with a low to good enantiomeric ratio. The direction and the level of the asymmetric induction were highly dependent on the type of protecting groups on the nitrogen and sulfur atoms.

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