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Issue 34, 2015
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D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

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Abstract

D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transformation in a highly selective fashion. The methodology employed consisted of three steps: diastereoselective formation of the oxazaphospholidine followed by subsequent selective cleavage of P–N and P–O bonds by reaction with two Grignard reagents. P-epimers oxazaphospholidines were prepared switching from a P(V) to a P(III) precursor, thus allowing for the synthesis of enantiomeric phosphine oxides. In addition, the chiral auxiliary could be recovered and efficiently recycled.

Graphical abstract: d-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

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Publication details

The article was received on 29 Jun 2015, accepted on 20 Jul 2015 and first published on 22 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01323B
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Citation: Org. Biomol. Chem., 2015,13, 9029-9034
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    D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

    A. D'Onofrio, L. Copey, L. Jean-Gérard, C. Goux-Henry, G. Pilet, B. Andrioletti and E. Framery, Org. Biomol. Chem., 2015, 13, 9029
    DOI: 10.1039/C5OB01323B

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