Sakakibara, Takuya Tokushima University
Someno, Takatoshi Tokushima University
Masui, Kana Tokushima University
amino phosphonic acid
A practical method for synthesizing chiral α-amino phosphonic acid derivatives was developed. Readily available and stable N-o-nitrophenylsulfenyl (Nps) imino phosphonate was utilized as a substrate for a highly enantioselective Friedel–Crafts-type addition of indole or pyrrole nucleophiles catalyzed by chiral phosphoric acid. The resulting adduct was easily converted to N-9-fluorenylmethyloxycarbonyl (Fmoc) amino phosphonic acid, which is useful for synthesizing peptides containing an amino phosphonic acid.
Chemistry- A European Journal
This is the peer reviewed version of the following article: T. Inokuma, T. Sakakibara, T. Someno, K. Masui, A. Shigenaga, A. Otaka, K.-i. Yamada, Chem. Eur. J. 2019, 25, 13829., which has been published in final form at https://doi.org/10.1002/chem.201903572. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
chemej_25_60_13829.pdf 2.44 MB