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Issue 42, 2012
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Asymmetric catalytic [4 + 1] annulations catalyzed by quinidine: enantioselective synthesis of multi-functionalized isoxazoline N-oxides

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Abstract

A highly regio-, chemo-, diastereo- and enantioselective organocatalytic [4 + 1] annulation of 2-halo-1,3-dicarbonyl compounds with Morita–Baylis–Hillman adducts catalyzed by commercially available, low cost quinidine for the preparation of synthetically unique and medicinally multi-functionalized isoxazoline N-oxides with three stereogenic centers including adjacent quaternary and tertiary stereocenters has been developed. Notably, the unexpected product ethyl 2-((tert-butyldimethylsilyl)oxy)-2-(5,5-diacetyl-3-((methylsulfonyl)oxy)-4-phenylisoxazolidin-3-yl)acetate (8) bearing a quaternary stereocenter and two tertiary stereocenters was obtained from the undocumented 5,5-diacetyl-3-(2-ethoxy-1-hydroxy-2-oxoethyl)-4-phenyl-4,5-dihydroisoxazole 2-oxide (4ba).

Graphical abstract: Asymmetric catalytic [4 + 1] annulations catalyzed by quinidine: enantioselective synthesis of multi-functionalized isoxazoline N-oxides

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Publication details

The article was received on 18 Jun 2012, accepted on 03 Sep 2012 and first published on 04 Sep 2012


Article type: Paper
DOI: 10.1039/C2OB26165K
Citation: Org. Biomol. Chem., 2012,10, 8471-8477
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    Asymmetric catalytic [4 + 1] annulations catalyzed by quinidine: enantioselective synthesis of multi-functionalized isoxazoline N-oxides

    Z. Guo, J. Xie, C. Chen and W. Zhu, Org. Biomol. Chem., 2012, 10, 8471
    DOI: 10.1039/C2OB26165K

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