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Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives

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Abstract

The successive addition of two different Grignard reagents to acyl cyanohydrins was performed with success by taking advantage of the low reactivity of alkynyl Grignard reagents. The experimental conditions were adjusted so that they were not reactive during the first addition step, but reactive only in the second one. The synthetic utility of the prepared compounds was validated by the preparation of chiral quaternary α-amino acids.

Graphical abstract: Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives

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Publication details

The article was received on 08 Dec 2017, accepted on 31 Jan 2018 and first published on 31 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03047A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives

    J. Caillé, F. Boukattaya, F. Boeda, M. S. M. Pearson-Long, H. Ammar and P. Bertus, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB03047A

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