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Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons.

Kai-Kai Wang¹, Yan-Li Li², Rongxiang Chen¹

¹School of Pharmacy, Xinxiang University, Xinxiang, Henan 453000, P. R. China.

The Journal of Organic Chemistry

|June 8, 2022

Summary

This study introduces an additive-free reaction forming complex spirooxindole derivatives from isatins and amino acids. The process creates multiple stereocenters with high yield and selectivity, offering tunable regioselectivity based on amino acid choice.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Stereoselective Synthesis

Background:

Spirooxindole scaffolds are prevalent in natural products and pharmaceuticals.
Efficient synthesis of complex spirooxindoles with multiple stereocenters remains a challenge.

Purpose of the Study:

To develop a novel additive-free [3 + 2] annulation strategy.
To synthesize functional and structurally complex 3,3'-pyrrolidinyl-spirooxindole derivatives.
To investigate the regioselectivity of the annulation reaction.

Main Methods:

Utilized isatins and amino acids (proline, thioproline, piperidine acid) with 2-styrylbenzoxazoles.
Employed a [3 + 2] annulation reaction under additive-free conditions.
Analyzed product structures and stereochemistry using analytical techniques.

Main Results:

Achieved high yields (up to 95%) and excellent diastereoselectivities (up to >25:1 dr).
Generated spirooxindole derivatives containing four contiguous and two quaternary stereogenic centers.
Demonstrated switchable regioselectivity (α- vs. γ-) based on the amino acid substrate.

Conclusions:

The developed method provides efficient access to complex spirooxindoles.
The reaction's regioselectivity can be controlled by substrate selection.
This work offers a valuable synthetic route for stereochemically rich spirooxindole compounds.