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

作者：Guo Zhi Wei; Xie Jian Wu^*; Chen Ce; Zhu Wei Dong

来源：Organic and Biomolecular Chemistry, 2012, 10(42): 8471-8477.

DOI：10.1039/c2ob26165k

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).

• 出版日期2012
• 单位浙江师范大学