アミノハロボランの有機合成化学における応用
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概要
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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, <I>N</I>-anilinophenylchloroboranes and <I>N</I>- alkylaminodichloroboranes reacted smoothly in the presence of triethylamine with benzaldehydes and isonitriles, probably via a cyclic transition state giving 2-aminobenzhydrols and 2-<I>N</I>-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.
- 社団法人 有機合成化学協会の論文
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