アミノハロボランの有機合成化学における応用
1981 年 39 巻 1 号 p. 39-50
詳細
1981 年 39 巻 1 号 p. 39-50
Aminohaloboranes, easily prepared from anilines, imines, ketones or alkylnitriles, and boron trichloride or diethylaminodichloroborane, were found to be a convenient species for C-C bond formation reaction in both aromatic and aliphatic series. Namely, N-anilinophenylchloroboranes and N- alkylaminodichloroboranes reacted smoothly in the presence of triethylamine with benzaldehydes and isonitriles, probably via a cyclic transition state giving 2-aminobenzhydrols and 2-N-alkylaminobenzaldehydes, respectively. A simple directed aldol reaction using vinylaminodichloroboranes and diethylaminovinyloxychloroboranes and a unique aldol-type reaction of alkylnitriles using diethylaminodichloroborane were performed under mild conditions. Using chiral vinylaminodichloroboranes made possible a very simple enantioselective aldol condensation reaction.
