BINOL-Salen-catalyzed highly enantioselective alkyne additions to aromatic aldehydes.
[structure: see text] The BINOL-Salen compound (-)-1 can catalyze the addition of both aryl- and alkylalkynes to aromatic aldehydes at room temperature with high enantioselectivity (86-97% ee). The conditions for this catalytic process are both mild and simple. Unlike most other BINOL-based catalysts, using ligand (-)-1 not only avoids heating or cooling but also does not require the addition of Ti(O(i)Pr)(4).
Li
Zi-Bo
ZB
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
Pu
Lin
L
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005029:Ethylenediamines / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000447:Aldehydes; D000480:Alkynes; C406944:BINOL, naphthol; D005029:Ethylenediamines; D008024:Ligands; D009284:Naphthols; C044736:phenylacetylene; C011452:disalicylaldehyde ethylenediamine; D015032:Zinc; D000114:Acetylene