Chiral macrocycle-catalyzed highly enantioselective phenylacetylene addition to aliphatic and vinyl aldehydes.
The 1,1'-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89-96% ee.
Li
Zi-Bo
ZB
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
Liu
Tian-Dong
TD
Pu
Lin
L
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000447:Aldehydes; C406944:BINOL, naphthol; D047028:Macrocyclic Compounds; D009284:Naphthols; D009942:Organometallic Compounds; D014753:Vinyl Compounds; C044736:phenylacetylene; C511262:dimethylzinc; D000114:Acetylene