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

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 onl...

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Veröffentlicht in:Organic & biomolecular chemistry 2018-02, Vol.16 (9), p.1519-1526
Hauptverfasser: Caillé, Julien, Boukattaya, Fatma, Boeda, Fabien, Pearson-Long, Morwenna S. M, Ammar, Houcine, Bertus, Philippe
Format: Artikel
Sprache:eng
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Zusammenfassung: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. The successive addition of two different Grignard reagents to acyl cyanohydrins was performed with success by using alkynyl Grignard reagents.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob03047a