期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 13, 页码 6629-6637出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00743
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资金
- University of Salerno (FARB)
- Regione Campania under POR Campania FESR [2007-2013-O.O. 2.1]
- IcFRC (International Center for Frontier Research in Chemistry) [Cyclo-CF2-ASYM]
- King Abdullah University of Science and technology
The fluoride-promoted vinylogous Mukaiyama-Michael reaction of 2-[(trimethylsilyl)oxy]furan with diverse alpha,beta-unsaturated ketones is described. The TBAF-catalyzed VMMR afforded high anti-diastereoselectivity irrespective of the solvents used. The KF/crown ethers catalytic systems proved to be highly efficient in terms of yields and resulted in a highly diastereoselective unprecedented solvent/catalyst switchable reaction. Anti-adducts were obtained as single diastereomers or with excellent diastereoselectivities when benzo-15-crown-5 in CH2Cl2 was employed. On the other hand, high syn-diastereoselectivities (from 73:27 to 96:4) were achieved by employing dicyclohexane-18-crown-6 in toluene. On the basis of DFT calculations, the catalysts/solvent-dependent switchable diastereoselectivities are proposed to be the result of loose or tight cation-dienolate ion pairs.
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