Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds

by Clay, David R.; McIntosh, Matthias C.

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.

Journal
Tetrahedron Letters
Volume
53
Issue
14
Year
2012
Start Page
1691-1694
URL
https://dx.doi.org/10.1016/j.tetlet.2011.12.123
ISBN/ISSN
1873-3581; 0040-4039
DOI
10.1016/j.tetlet.2011.12.123