Toward improving the chemistry of N-acyliminium ions: nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)

Raja Ben Othman; Till Bousquet; Anthony Fousse; Mohamed Othman; Vincent Dalla

doi:10.1021/ol050576z

Toward improving the chemistry of N-acyliminium ions: nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)

Org Lett. 2005 Jul 7;7(14):2825-8. doi: 10.1021/ol050576z.

Authors

Raja Ben Othman¹, Till Bousquet, Anthony Fousse, Mohamed Othman, Vincent Dalla

Affiliation

¹ Unité de Recherche en Chimie Organique et Macromoléculaire, Faculté des Sciences et Techniques de l'Université du Havre, France.

PMID: 15987146
DOI: 10.1021/ol050576z

Abstract

[reaction: see text] Nucleophilic substitution reactions of racemic and chiral 5-acetoxy-, 5-ethoxy-, and 5-methoxypyrrolidin-2-ones by silicon-based nucleophiles were efficiently catalyzed by TIPSOTf. This process was found to be general and accommodates a broad range of substrate-nucleophile combinations.