Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds
by Clay, David Ross; McIntosh, Matt 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. (C) 2012 Elsevier Ltd. All rights reserved.
- Journal
- Tetrahedron Letters
- Volume
- 53
- Issue
- 14
- Year
- 2012
- Start Page
- 1691
- ISBN/ISSN
- 1873-3581; 0040-4039
- PMID
- 22707800
- DOI
- 10.1016/j.tetlet.2011.12.123