Asymmetric synthesis of spirocyclic pyrrolidines and tetrahydrofurans by chiral aldol reactions and phenylthio migration

Article abstract of DOI:10.1016/0040-4039(91)80244-Z

Highly enantioselective aldol reactions of the boron enolate of (S)-N-propionyl-4-(phenylmethyl)-2-oxazolidinone with α-phenylthio cycloalkanecarbaldehydes were achieved. Cyclisation of the chiral phenylthiosulphonamide and diols gave the title compounds in excellent yields and enantiomeric excess.