Intramolecular ring-opening from a CO2-derived nucleophile as the origin of selectivity for 5-substituted oxazolidinone from the (salen)Cr-catalyzed [aziridine + CO2] coupling

Debashis Adhikari, Aaron W. Miller, Mu Hyun Baik*, Sonbinh T. Nguyen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

The (salen)Cr-catalyzed [aziridine + CO2] coupling to form oxazolidinone was found to exhibit excellent selectivity for the 5-substituted oxazolidinone product in the absence of any cocatalyst. Quantum mechanical calculations suggest that the preferential opening of the substituted C-N bond of the aziridine over the unsubstituted C-N bond is a key factor for this selectivity, a result that is supported by experiment with several phenyl-substituted aziridines. In the presence of external nucleophile such as dimethyl aminopyridine (DMAP), the reaction changes pathway and the ring-opening process is regulated by the steric demand of the nucleophile.

Original languageEnglish (US)
Pages (from-to)1293-1300
Number of pages8
JournalChemical Science
DOIs
StatePublished - Feb 1 2015

ASJC Scopus subject areas

  • Chemistry(all)

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