期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2010, 期 5, 页码 972-980出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901159
关键词
Tetrahydroisoquinoline; Amino alcohols; Ruthenium; Hydrogenation; Asymmetric catalysis
资金
- National Research Foundation (South Africa) [2073251]
- SA/Swedish Research Links Programme
- Aspen Pharmacare, SA
Tetrahydroisoquinoline (TIQ) derivatives exhibit good biological activity. However, utilization of TIQ compounds in asymmetric catalysis is limited. This paper presents a series of TIQ derivatives in asymmetric transfer hydrogenation (ATH) reactions. Chiral TIQ amino alcohol ligands were synthesized and screened for the ATH reaction of aromatic ketones. The effect of a cis- and trans-phenyl substitution at the C-1 position on the ligand backbone was investigated both experimentally and computationally. The results showed that the trans orientation on the TIQ scaffold yields higher turnover rates with a selectivity of 94% ee obtained at room temperature with an Ru complex. The cis isomer results in a high turnover rate with no selectivity. The trans isomer gave 99% ee at lower temperatures. Furthermore, it was observed that substitution at the C-3-alpha position results in a drop of the enantioselectivity and the reactivity of the catalyst.
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