有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
イソシアナートを用いる複素環合成におけるスズ種の触媒作用
芝田 育也
著者情報
ジャーナル 認証あり

2017 年 75 巻 7 号 p. 757-767

詳細
抄録

Synthesis of nitrogen heterocycles using isocyanates was achieved by organotin reagents and catalysts. The reactions proceeded via intramolecular alkylation through terminally functionalized tin species. Thus terminally halogenated, enone-substituted and carbonyl substituted tin alkoxides have been provided as key intermediates. Such tin species could be generated by tin-mediated selective reactions, the ring cleavage of halo lactones and the addition to functionalized carbonyl compounds. These equimolar reactions induced to tin alkoxide-catalyzed reactions, that is, catalytic annulation of isocyanates with α-hydroxyl carbonyls, glycolide, lactide. In particular, optically pure nitrogen heterocycles were obtained directly from easily available plant-derived chiral sources, lactides. Further, tin halide-catalyzed reactions could be developed, that is, catalytic annulation of isocyanates with epoxides, 2-methyleneaziridines and cyclopropanes. This article includes author’s development of tin promoted synthesis of nitrogen heterocycles using isocyanates.

著者関連情報
© 2017 社団法人 有機合成化学協会
前の記事 次の記事
feedback
Top