1. Pyrrolidine-oxadiazolone conjugate as new organocatalyst for asymmetric aldol condensation.
- Author
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Mahato, Chandan K., Mandal, Subhro, Kundu, Mrinalkanti, and Pramanik, Animesh
- Subjects
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ALDOL condensation , *STEREOSELECTIVE reactions , *ALDOLS , *AROMATIC aldehydes , *ORGANIC solvents , *SOLUBILITY , *NITROALDOL reactions , *CONDENSATION reactions - Abstract
A proline-based, chiral bi-functional organocatalyst containing both pyrrolidine and oxadiazolone heterocycle, has been successfully applied for stereoselective aldol reactions. The replacement of polar -COOH group of proline with bioisostere oxadiazolone ring provides excellent solubility of this catalyst in various organic solvents compared to low soluble proline. As a result, the organocatalyst effectively catalyzed the asymmetric condensation reaction between differently substituted aromatic aldehydes and various symmetrical and unsymmetrical ketones to produce the corresponding aldol products with excellent stereoselectivities (dr: 97:3, ee >99.9%) at room temperature in open-air. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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