Organocatalytic Enantio- and Diastereoselective Synthesis of Dispirooxindole Derivatives with Adjacent Spirocyclic
Raquel Hidalgo-León1, José Trujillo-Sierra1, José Miguel Sansano1
1Departamento de Química Orgánica, Centro de Innovación en Química Avanzada (ORFEO-CINQA) and Institute of Organic Synthesis, Universidad de Alicante, Ctra. Alicante-San Vicente s/n, Alicante 03080, Spain.
Abstract:
The highly diastereo- and enantioselective organocatalytic synthesis of six-membered ring dispirocyclohexane oxindole derivatives with adjacent spirocyclic centers via [4 + 2] cycloadditions is described. The combination of a cinchonidine-derived primary amine catalyst with p-methylbenzoic acid as a cocatalyst allows access to a broad range of dispirocyclohexane oxindoles. The influence of substituents on the reaction outcome was thoroughly evaluated, including those at the N-position of the oxindole and those at the terminal carbon of the C═C double bond.
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