Zinc-Mediated Double Addition on Functionalized Nitriles

Abstract Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic allylation occurs twice, due to an in...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2019-03, Vol.51 (6), p.1329-1341
Main Authors: Caillé, Julien, Pantin, Mathilde, Boeda, Fabien, Pearson-Long, Morwenna S. M., Bertus, Philippe
Format: Article
Language:English
Subjects:
Chemical Sciences
feature
Organic chemistry
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Summary:Abstract Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic allylation occurs twice, due to an intermediate transfer of the carbonyl moiety onto the nitrogen atom. The chemoselectivity of the reaction allows the presence of various functionalities and in the case of carbonate derivatives, the nature of the final product was modulated by kinetic control, giving selectively hydroxyamides or cyclic carbamates.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1611704