1,4-Addition of arylboronic acids to β-aryl-α,β-unsaturated ketones and esters catalyzed by a rhodium(I)–chiraphos complex for catalytic and enantioselective synthesis of selective endothelin A receptor antagonists

摘要: Abstract An enantioselective synthesis of acyclic β-diaryl ketones and esters via 1,4-addition arylboronic acids to β-aryl-α,β-unsaturated or is described. The complex in situ prepared from [Rh(nbd) 2 ]BF 4 chiraphos was found be an excellent catalyst achieve high enantioselectivities a range 83–89% ee for the ketone derivatives 78–94% tert -butyl β-arylacrylate derivatives. protocol provided catalytic method selective endothelin A receptor antagonists ( 7 , 8 ) reported by SmithKline Beecham Merck–Banyu. enantioselection mechanism efficiency ligand are discussed on basis results DFT computational studies modes coordination enone substrates to the phenylrhodium(I)–( S )-chiraphos complex.