Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.
The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction. [reaction: see text]
Gao
Ge
G
Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.
Moore
David
D
Xie
Ru-Gang
RG
Pu
Lin
L
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000447:Aldehydes; D007202:Indicators and Reagents; C044736:phenylacetylene; D000114:Acetylene