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Issue 22, 2014
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Functionalization of an sp3 C–H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles

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Abstract

A diastereoselective synthesis of pyrrolidinooxazolidines was achieved by a metal-free, base-promoted reaction of pyrrolidine and aromatic aldehydes under microwave irradiation. The rare functionalization of an sp3 C–H bond probably results from an in situ generated azomethine ylide that undergoes cycloaddition with aldehydes.

Graphical abstract: Functionalization of an sp3 C–H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles

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Publication details

The article was received on 19 Jan 2014, accepted on 28 Jan 2014 and first published on 28 Jan 2014


Article type: Communication
DOI: 10.1039/C4CC00454J
Citation: Chem. Commun., 2014,50, 2951-2953
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    Functionalization of an sp3 C–H bond via a redox-neutral domino reaction: diastereoselective synthesis of hexahydropyrrolo[2,1-b]oxazoles

    M. Rahman, A. K. Bagdi, S. Mishra and A. Hajra, Chem. Commun., 2014, 50, 2951
    DOI: 10.1039/C4CC00454J

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