Ruthenium BINAP Catalyzed Alcohol C H tert Prenylation via 1,3 Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation.
The chiral ruthenium complex formed in situ from (TFA)2Ru(CO)(PPh3)2 and (R) BINAP is found to catalyze the enantioselective C C coupling of diverse primary alcohols with the 1,3 enyne, TMSCCC(Me) CH2, to form secondary homopropargyl alcohols bearing gem dimethyl groups. All reagents for this byproduct free coupling are inexpensive and commercially available, making this protocol a practical alternative to stoichiometric carbanions in enantioselective carbonyl reverse prenylation.
Journal of the American Chemical Society