What question did this study set out to answer?

The research aims to develop a highly selective method for synthesizing dispirooxindole derivatives.

April 8, 2026The Journal of Organic Chemistry0 citationsOpen Access

Organocatalytic Enantio- and Diastereoselective Synthesis of Dispirooxindole Derivatives with Adjacent Spirocyclic Centers via 4 + 2 Cycloadditions

RHRaquel Hidalgo-León JTJosé Enrique Trujillo-Sierra JSJosé M. Sansano

Key Points

The research aims to develop a highly selective method for synthesizing dispirooxindole derivatives.
Employs an organocatalytic approach using cinchonidine-derived primary amine and p-methylbenzoic acid.
Utilizes [4 + 2] cycloadditions to form six-membered ring structures.
Evaluates the impact of different substituents on reaction outcomes.
Successfully synthesizes a wide range of dispirocyclohexane oxindoles.
Achieves high levels of diastereo- and enantioselectivity.
Demonstrates variation in outcomes based on substituents at the N-position and terminal carbon.

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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