Asymmetric synthesis catalyzed by chiral ferrocenylphosphine transition metal complexes. 10 gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate

Article abstract of DOI:10.1016/S0040-4020(01)88870-0

Optically active ferrocenylbisphosphine ligands containing 2-(dialkylamino)ethylamino group on the ferrocenylmethyl position have been prepared and used for the gold(I)-catalyzed asymmetric aldol reaction of isocyanoacetate with aldehydes. Six-membered ring amines, such as morpholino or piperidino group, at the terminal of the side chain were most stereoselective to give optically active trans-4- methoxycarbonyl-5-alkyl-2-oxazolines (up to 97% ee) with high enantio- and diastereoselectivity in a quantitative yield.