Highly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Salts
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2023-04Autor
Tallarida, Matteo A.
Olivito, Fabrizio
Navo, Claudio D.
Algiero, Vincenzo
Jiritano, Antonio
Costanzo, Paola
Poveda, Ana
Moure, Maria J.
Maiuolo, Loredana
Jiménez Oses, Gonzalo
De Nino, Antonio
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Organic Letters 25(17) : 3001-3006 (2023)
Resumen
The synthesis of polysubstituted spirocyclopropyl oxindoles using a series of rare-earth metal (REM) salts is reported. REMs, in particular Sc(OTf)3, allowed access to the target compounds by a multicomponent reaction with high diastereoselectivity (≤94:6:0:0). Density functional theory calculations on the model reaction are consistent with the observed selectivity and revealed that the special coordinating capabilities and the oxophilicity of the metal are key factors in inducing the formation of one main diastereoisomer.