Graduate School of Pharmaceutical Sciences, Osaka University , 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
J Org Chem. 2017 Aug 18;82(16):8733-8742. doi: 10.1021/acs.joc.7b01288. Epub 2017 Aug 9.
Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives undergo a cycloisomerization in the presence of a well-defined ruthenium hydride to give a 2,3-disubstitued indole. The vinyl and silylmethyl substituents on the 2- and 3-positions of the indole can be easily converted to other functional groups.
环化异构化是一种原子经济性的过程，可将二烯和烯炔转化为环状分子。迄今为止，酰胺基和硅基炔烃之间的环化异构化尚未得到探索。我们发现，在定义明确的钌氢化物存在下，N-酰基-N-乙烯基-2-硅基炔基苯胺衍生物发生环化异构化，生成 2,3-取代的吲哚。吲哚的 2-和 3-位上的乙烯基和硅甲基取代基可以很容易地转化为其他官能团。
