Boron azaenolates of chiral oxazolines: Synthesis of optically active formyl oxiranes

Article abstract of DOI:10.1016/S0040-4039(99)01480-X

Boron azaenolates 2 and 8 from the optically active chloromethyloxazolines 1 and 7 have been found to couple with ketones in a highly diastereoselective fashion, which depends markedly upon the geometry (Z) of the azaenolates and the nature of the ligands which are present on the boron atom, in good accordance with semiempirical calculations (AM1).