Highly Enantioselective Construction of Polycyclic Spirooxindoles by Organocatalytic 1,3-Dipolar Cycloaddition of 2-Cyclohexenone Catalyzed by Proline-Sulfonamide

The enantioselective 1,3‐dipolar cycloaddition of 2‐cyclohexene‐1‐one and azomethine ylides generated in situ from isatins and amino esters was developed by employing prolinosulfonamides as the catalyst. Consequently, novel polycyclic spirooxindole scaffolds with three contiguous stereocenters were...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-09, Vol.2014 (26), p.5700-5704
Main Authors: Xiao, Jun-An, Liu, Qi, Ren, Ji-Wei, Liu, Jian, Carter, Rich G., Chen, Xiao-Qing, Yang, Hua
Format: Article
Language:English
Subjects:
Alkaloids
Cycloaddition
Nitrogen heterocycles
Organocatalysis
Spiro compounds
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Summary:The enantioselective 1,3‐dipolar cycloaddition of 2‐cyclohexene‐1‐one and azomethine ylides generated in situ from isatins and amino esters was developed by employing prolinosulfonamides as the catalyst. Consequently, novel polycyclic spirooxindole scaffolds with three contiguous stereocenters were prepared in high yield (up to 95 %) with excellent diastereo‐ (>20:1 dr) and enantioselectivity (up to 99 % ee). The highly enantioselective construction of polycyclic spirooxindoles through 1,3‐dipolar cycloaddition of cyclohexenone with azomethine ylides is achieved by employing prolinosulfonamides as the catalyst. This catalytic system essentially benefits from iminium activation and hydrogen‐bonding formation induced by the prolinosulfonamides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402953