BRUNNER, H and FISCH, K (1993) ASYMMETRIC CATALYSIS .82. ENANTIOSELECTIVE HYDRATION OF 4-OXOISOPHORONE. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 456 (1). pp. 71-75. ISSN 0022-328X,
Full text not available from this repository.Abstract
Enantioselective hydrogenation of 4-oxoisophorone 1. catalysed by BINAP-Ru(II) complexes, gives the corresponding saturated diketone 2 in 80% chemical yield and 50% enantiomeric excess. By repeated crystallisation from petroleum ether/dichloromethane 4/1 the diketone 2 is obtained optically pure in 25% total yield. The monoalcohol 3 is formed as a byproduct of the hydrogenation. The formation of 3 can be suppressed by using the monomethyl-enol ether 4 as a substrate. Catalytic hydrogenation of 4 in methanol gives exclusively the dimethylketal 5, which upon acidic hydrolysis is transformed into the diketone 2 in 50% ee.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | UNSATURATED KETONES; HYDROGENATION; COMPLEXES; BINAP; |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:42 |
| URI: | https://pred.uni-regensburg.de/id/eprint/53821 |
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