ヘテロ原子-ハロゲン結合を活用する簡便な合成手法の開発

概要

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Heteroatom–halogen bonds were successfully utilized for efficient and convenient synthesis of heterocycles and aminohalogenated compounds from readily available reagents. The direct aziridination of olefins with N–chloro–N–sodio–p–toluenesulfonamide (chloramines–T: CT) in the presence of iodine catalyst has been achieved, and the method was applied to a green process using silica–water as the reaction media. N–Chloro–N–sodiocarbamates reacted with electron–deficient olefins in the presence of a phase transfer catalyst to give the corresponding aziridines, and the method was applied to the asymmetric synthesis. Fullerene, C60, was also aziridinated by using active reagents containing N–X bonds, and the resulting aziridinofullerenes underwent a unique rearrangement to azafulleroids. Moreover, unique aminohalogenation of olefins utilizing chloramines–T and bromamine–T under an atmosphere of carbon dioxide was also revealed. Treatment of alkenylamides with tert–butyl hypoiodite led to the production of various N–heterocycles. Iodination of readily available sulfonamides or carboxamides with tert–butyl hypoiodite generated reactive N–iodinated amides, which reacted with olefins to give aziridines or oxazolines.
2009-10-01