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

Zhi-Wei Guo, Jian-Wu Xie, Ce Chen, Wei-Dong Zhu

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, PR of China.

Organic & biomolecular chemistry 2012 Nov 14

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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).

Citation

Zhi-Wei Guo, Jian-Wu Xie, Ce Chen, Wei-Dong Zhu. Asymmetric catalytic [4 + 1] annulations catalyzed by quinidine: enantioselective synthesis of multi-functionalized isoxazoline N-oxides. Organic & biomolecular chemistry. 2012 Nov 14;10(42):8471-7