Highly Enantioselective Construction of Polycyclic Spirooxindoles by Organocatalytic 1,3-Dipolar Cycloaddition of 2-Cyclohexenone Catalyzed by Proline-Sulfonamide
作者： Jun-An Xiao , Qi Liu , Ji-Wei Ren , Jian Liu , Rich G. Carter
关键词: Amino esters 、 Organic chemistry 、 Organocatalysis 、 Cycloaddition 、 Enantioselective synthesis 、 Sulfonamide 、 1,3-Dipolar cycloaddition 、 Stereocenter 、 Isatin 、 Chemistry
摘要: The enantioselective 1,3-dipolar cycloaddition of 2-cyclohexene-1-one and azomethine ylides generated in situ from isatins amino esters was developed by employing prolinosulfonamides as the catalyst. Consequently, novel polycyclic spirooxindole scaffolds with three contiguous stereocenters were prepared high yield (up to 95 %) excellent diastereo- (>20:1 dr) enantioselectivity 99 % ee).
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