Enantioselective synthesis of propargylamines through Zr-catalyzed addition of mixed alkynylzinc reagents to arylimines.
[reaction: see text] Addition of mixed alkynylzinc reagents to various arylimines is catalyzed by chiral amino acid-based ligand 1 and Zr(Oi-Pr)(4).HOi-Pr to afford chiral propargylamines in up to 90% ee. Oxidative removal of the o-anisidyl group affords the free amine, which can then be acylated.
Traverse
John F
JF
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Hoveyda
Amir H
AH
Snapper
Marc L
ML
D000215:Acylation; D000480:Alkynes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000138:chemical synthesis*; D008024:Ligands; D010084:Oxidation-Reduction; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011437:Propylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015040:Zirconium
D000480:Alkynes; D000596:Amino Acids; D000814:Aniline Compounds; D007097:Imines; D008024:Ligands; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline; D015040:Zirconium