Organocatalytic chemoselective monoacylation of 1,n-linear disulfonamides |
| |
Authors: | Keisuke Yoshida Atsushi Hirata Hisashi Hashimoto Ayumi Imayoshi Yoshihiro Ueda Takumi Furuta Takeo Kawabata |
| |
Institution: | Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan |
| |
Abstract: | Predominant monoacylation of 1,n-linear disulfonamides took place in the presence of pyrrolidinopyridine-type organocatalysts when the chain length of the linear disulfonamides was n = 3, 4, or 5 (monoacylate/diacylate = up to 44). The chemoselectivity of the competitive acylation between N,N′-ditosyl-1,5-pentanediamine (n = 5) and N,N′-ditosyl-1,3-propanediamine (n = 3) was found to be 36, favoring the former substrate. Different chain length by only one carbon atom was discriminated in the competitive acylation between N,N′-ditosyl-1,5-pentanediamine (n = 5) and of N,N′-ditosyl-1,4-butanediamine (n = 4) with the relative acylation rate of 16 in the presence of the organocatalyst. |
| |
Keywords: | Organocatalyst Acylation Chemoselectivity Diamine Molecular recognition |
本文献已被 ScienceDirect 等数据库收录! |
|