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Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds.

ABSTRACT: 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 vs 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.

SUBMITTER: Clay DR

PROVIDER: S-EPMC3374411 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds.

Clay David R DR McIntosh Matthias C MC

Tetrahedron letters 20120114 14

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 vs 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. ...[more]

PMID: 22707800

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