Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds

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• 作者：David R. Clay ; Matthias C. McIntosh ; ^{mcintosh@uark.edu}
• 关键词：Transfer hydrogenation ; Noyori ; Asymmetric ; meso
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：4 April, 2012
• 年：2012
• 卷：53
• 期：14
• 页码：1691-1694
• 全文大小：471 K

文摘

Over the course of developing a multigram scale preparation of epoxy quinol 1 via asymmetric transfer hydrogenation (ATH) using the Noyori Ru(arene)(S,S-TsDPEN) catalysts, we observed several unexpected phenomena, including (i) chemoselective alkene versus ketone reduction of an enedione, (ii) a significant arene ligand effect (p-cymene vs mesitylene) on the reaction pathway, and (iii) solvent-based reversal of the sense of enantioinduction.