HYDROBORATION D'AMINES INSATUREES. XI.REGIO- ET STEREOSELECTIVITE DES HYDRURES DU BORE VIS A VIS D'AMINES PROPARGYLIQUES N-PHOSPHORYLEES

Article abstract of DOI:10.1016/S0022-328X(00)98991-5

The regioselectivity and the stereoselectivity of the hydroboration of N-alkylallylphosphoramide was examined.This study shows the preferential formation of γ-boron derivatives (90 to 100percent) and the excellent stereospecificity of the reaction (100percent (Z) configuration).The P^IV-N bond hinders the nitrogen-boron coordination which is responsible for the anomalous behavior of N-propargylic amines towards hydroboration and allows the same regio- and stereo-selectivity as for alkynes.The iodination of boron derivatives leads, with good yields, to N-phosphoryl-β-ethylenic amines.