Alkynenitriles: chelation-controlled conjugate additions.
[reaction: see text] Chelation between gamma-hydroxybutynenitrile and Grignard reagents triggers a particularly facile anionic conjugate addition reaction. Structurally diverse Grignard reagents add with equal efficiency, providing an intermediate anion that stereoselectively alkylates benzaldehyde in an overall addition-alkylation reaction.
Fleming
Fraser F
FF
Department of Chemistry and Biochemistry, Duquesne University, Pittsburgh, Pennsylvania 15282-1530, USA. flemingf@duq.edu
Gudipati
Venugopal
V
Steward
Omar W
OW
D000480:Alkynes / Q000138:chemical synthesis*; D002614:Chelating Agents / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000480:Alkynes; D002614:Chelating Agents; D007202:Indicators and Reagents; D009570:Nitriles