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Highly Enantioselective Construction of Polycyclic Spirooxindoles by Organocatalytic 1,3‐Dipolar Cycloaddition of 2‐Cyclohexenone Catalyzed by Proline‐Sulfonamide
Author(s) -
Xiao JunAn,
Liu Qi,
Ren JiWei,
Liu Jian,
Carter Rich G.,
Chen XiaoQing,
Yang Hua
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402953
Subject(s) - enantioselective synthesis , chemistry , stereocenter , sulfonamide , cycloaddition , organocatalysis , catalysis , 1,3 dipolar cycloaddition , yield (engineering) , combinatorial chemistry , organic chemistry , cyclohexenone , stereochemistry , materials science , metallurgy
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 ).