Cinchona Alkaloid‐Derived Thiourea‐Catalyzed Diastereo‐ and Enantioselective [3+2] Cycloaddition Reaction of Isocyanoacetates to Isatins: A Facile Access to Optically Active Spirooxindole Oxazolines
- 30 April 2013
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 355 (7) , 1277-1283
Abstract
An efficient diastereo‐ and enantioselective [3+2] cycloaddition reaction of α‐aryl isocyanoacetates to isatins catalyzed by a quinine‐derived bifunctional amine‐thiourea‐bearing sulfonamide as multiple hydrogen‐bonding donor catalyst has been investigated. The corresponding adducts, which bear a spirocyclic quaternary stereocenter at the C‐3 position of the oxindole, were obtained in good yields (51–95%), high diastereoselectivities (up to >20:1 dr) and good to excellent enantioselectivities (up to 97% ee).Keywords
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