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.
Highly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Salts
Matteo A. Tallarida
Membro del Collaboration Group
;Fabrizio OlivitoMembro del Collaboration Group
;Vincenzo AlgieriMembro del Collaboration Group
;Antonio JiritanoMembro del Collaboration Group
;Paola CostanzoMembro del Collaboration Group
;Loredana MaiuoloMembro del Collaboration Group
;Antonio De Nino
Membro del Collaboration Group
2023-01-01
Abstract
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.File in questo prodotto:
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