Generation of multifunctionalized nucleophilic carbenes

为了开发一种在低温下生成亲核卡宾的方法，我们研究了一种由β-甲硅烷基-α，β-环氧醛衍生的亚胺盐，该亚胺盐可以通过亚胺碳原子上的质子去质子化、环氧化物开环和所得α-甲硅烷基醇盐的Brook重排生成亲核卡宾。我们设计了一种制备底物的方法，并发现需要对底物进行一些结构修饰才能成功地生成亲核卡宾。在此过程中，我们还发现了一类新的偶极子1，n-偶极（n → 3），它可以作为合成复杂分子的重要中间体。

With the aim of developing a method that allows the generation of nucleophilic carbenes at a cryogenic temperature, we focused on an iminium salt derived from β-silyl-α,β-epoxyaldehydes, which can potentially generate a nucleophilic carbene via deprotonation of a proton on an iminium carbon atom, ring-opening of epoxide and Brook rearrangement of the resulting α-silyl alkoxide. We devised a method for the preparation of the substrates and found that some structural modification of the substrates is required to successfully generate a nucleophilc carbene. During the attempt, we also found that 1,n-dipole (n ≠3), a new class of synthons, can serve important intermediates in the synthesis of complex molecules.