Palladium-catalyzed regioselective domino cyclization of cyclohexadienones.
A mild and efficient Pd-catalyzed arylative domino carbocyclization of cyclohexadienone-containing 1,6-enynes is described. The reaction tolerates a variety of functionalized boronic acids to afford a cis-fused bicyclic framework containing an α,β-unsaturated ketone with excellent regio- and diastereoselectivity in good yields. The tandem process proceeds with β-arylation of propargylic ether followed by conjugate addition of a vinyl palladium intermediate and subsequent protonolysis of a palladium enolate.
†Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Akondi Srirama
AS
Murthy
†Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Sangeetha
S
Donikela
‡Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India.
Cirandur Suresh
CS
Reddy
†Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Rambabu
R
Chegondi