Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 6, Pages 1329-1341Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611704
Keywords
allylation; nitriles; nucleophilic addition; organometallic reagents; tertiary carbinamines; zinc
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Funding
- Ministere de l'enseignement superieur et de la recherche
- Universite Bretagne Loire
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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.
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