116763-08-7Relevant articles and documents
Microwave-assisted ring-closing metathesis of diallylamines: a rapid synthesis of pyrrole and pyrroline derivatives
Yang, Qian,Li, Xin-Yong,Wu, Hong,Xiao, Wen-Jing
, p. 3893 - 3896 (2006)
The ring-closing metathesis (RCM) reactions of diallylamines occurred under controlled microwave irradiation. In addition to the high reaction rate, the key features of the reaction are that it can be carried out without deactivation of the substrates and
Nonenzymatic, enantioconvergent dynamic kinetic resolution (DKR) of racemic 2-(1H-pyrrol-1-yl)alkanoic acids as α-amino acid equivalents
Tokumaru, Eri,Tengeiji, Atsushi,Nakahara, Takayoshi,Shiina, Isamu
supporting information, p. 1768 - 1770 (2016/02/18)
We report an effective dynamic kinetic resolution (DKR) system of racemic 2-(1H-pyrrol-1-yl)alkanoic acids, which consists of a rapid racemization step via an activating substrate and an enantio-discriminating step via catalytic esterification. The combination of pivalic anhydride as an activating agent, bis(α-naphthyl)methanol as an achiral alcohol, (R)-BTM as a chiral acyl-transfer catalyst, and Hunig's base converted racemic 2-(1H-pyrrol-1-yl)alkanoic acids to the corresponding chiral carboxylates, which can be transformed into chiral α-amino acid derivatives with maintained high enantiopurity.
Peptide Synthesis Using the Pyrrole Ring as an Amino Protecting Group
Kashima, Choji,Maruyama, Tatsuya,Harada, Kazuo,Hibi, Shigeki,Omote, Yoshimori
, p. 601 - 645 (2007/10/02)
The utility of a pyrrole ring as an amino protecting group for amino acids in peptide synthesis has been studied.The N-termini of various amino acids (1) were protected with a pyrrole ring by treatment with 2,5-dimethoxytetrahydrofuran (10) to give 2-substituted 2-(1-pyrrolyl)acetic acids (11).The peptide bond between (11) and amino acid methyl ester (2) was formed using N,N'-dicyclohexylcarbodiimide, and the pyrrole ring was cleaved by ozonolysis and hydrolysis without the cleavage of a peptide bond to give the corresponding dipeptide compounds (26) in good yields.