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Issue 102, 2014
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Ring-opening of enantiomerically pure oxa-containing heterocycles with phosphorus nucleophiles

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Abstract

Various oxa-containing heterocycles (i.e. enantiopure epoxide- and oxetane-based substrates) were subjected to ring-opening with phosphorus nucleophiles. The ring-opening reactions proceeded smoothly and the resulting 1,2-, and 1,3-phosphino alcohols were efficiently isolated as stable borane complexes. These derivatives arise from regio- and stereocontrolled syntheses based on ring-opening processes of oxa-containing heterocycles. The regio- and stereochemistry of the resulting chiral products were unequivocally confirmed in many cases via single-crystal X-ray diffraction analysis.

Graphical abstract: Ring-opening of enantiomerically pure oxa-containing heterocycles with phosphorus nucleophiles

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Publication details

The article was received on 15 Sep 2014, accepted on 29 Oct 2014 and first published on 30 Oct 2014


Article type: Paper
DOI: 10.1039/C4RA10432C
Citation: RSC Adv., 2014,4, 58440-58447
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    Ring-opening of enantiomerically pure oxa-containing heterocycles with phosphorus nucleophiles

    H. Fernández-Pérez, P. Etayo, J. L. Núñez-Rico, B. Balakrishna and A. Vidal-Ferran, RSC Adv., 2014, 4, 58440
    DOI: 10.1039/C4RA10432C

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