Si- and C-Functional Organosilicon Building Blocks for Synthesis Based on 4-Silacyclohexan-1-ones Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP (2,6-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl)
作者:Marcel Geyer、Olle Karlsson、Johannes A. Baus、Eric Wellner、Reinhold Tacke
DOI:10.1021/acs.joc.5b00774
日期:2015.6.5
trimethoxypropylsilane. All of these compounds represent C-functional (R2C═O, R2C═N–OH, R–NH(C═O)–R, R2NH, or R3C–Br) silicon-containing heterocycles that contain Si–MOP, Si–DMOP, or Si–TMOP moieties (MOP = 4-methoxyphenyl; DMOP = 2,6-dimethoxyphenyl; TMOP = 2,4,6-trimethoxyphenyl), which can be cleaved under mild conditions by protodesilylation. As a proof of principle, compounds 3a–3c were transformed quantitatively
4-Silacyclohexan-1-one 1a - 1c,4-silacyclohexan-1-one肟2a - 2c,1,4-azasilepan-7-ones 3a - 3c,1,4-azasilepanes 4a - 4c和2-bromo-从三甲氧基丙基硅烷开始,通过多步合成制备4-硅环己酮-1-酮5a和5b。所有这些化合物均代表C-官能团(R 2 C = O,R 2 C = N–OH,R–NH(C═O)–R,R 2 NH或R 3C–Br)的含硅杂环,其中含有Si–MOP,Si–DMOP或Si–TMOP部分(MOP = 4-甲氧基苯基; DMOP = 2,6-二甲氧基苯基; TMOP = 2,4,6-三甲氧基苯基),在温和的条件下可以通过protodesilylation裂解。作为原理证明,将化合物3a - 3c定量并选择性地转化为氯硅烷6(在二氯甲烷中用氯化氢处理)。因此,碳和硅官能化合物1a