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Issue 9, 2018
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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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Supplementary files

Article information


Submitted
08 Dec 2017
Accepted
31 Jan 2018
First published
31 Jan 2018

Org. Biomol. Chem., 2018,16, 1519-1526
Article type
Paper

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, 16, 1519
DOI: 10.1039/C7OB03047A

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