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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

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RHRaquel Hidalgo-LeónJTJosé Enrique Trujillo-SierraJSJosé 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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Cite This Study

Hidalgo-León et al. (2026) studied this question.

synapsesocial.com/papers/69d5f0d774eaea4b11a7a53fhttps://doi.org/10.1021/acs.joc.6c00103
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