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Direct Guanylation of Amino Groups by Cyanamide in Water: Catalytic Generation and Activation of Unsubstituted Carbodiimide by Scandium(III) Triflate

Kazuki Tsubokura, Takayuki Iwata, Misako Taichi, Almira Kurbangalieva, Koichi Fukase, Yoichi Nakao, Katsunori Tanaka*

*Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan, Email: kotzenoririken.jp

K. Tsubokura, T. Iwata, M. Taichi, A. Kurbangalieva, K. Fukase, Y. Nakao, K. Tanaka, Synlett, 2014, 25, 1302-1306.

DOI: 10.1055/s-0033-1341080 (free Supporting Information)


Abstract

An efficient guanylation of various amines with cyanamide proceeds in the presence of catalytic amounts of scandium(III) triflate under mild conditions in water without using preactivated guanylation reagents. Therefore, the method has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds.

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Key Words

guanylation, Sc(OTf)3, cyanamide, activated carbodiimide


ID: J60-Y2014