80687-79-2Relevant articles and documents
A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries
Itoh, Takashi,Miyazaki, Michiko,Ikeda, Sachiko,Nagata, Kazuhiro,Yokoya, Masashi,Matsuya, Yuji,Enomoto, Yasuko,Ohsawa, Akio
, p. 3527 - 3536 (2007/10/03)
9-(S)-Pyroglutaminyl-β-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products.
A Convenient Preparation of N-Acylpyroglutamic Acid
Imaki, Katsuhiro,Niwa, Haruki,Sakuyama, Shigeru,Okada, Takanori,Toda, Masaaki,Hayashi, Masaki
, p. 2699 - 2701 (2007/10/02)
Pyroglutamic acid reacted with acyl chloride in the presence of triethylamine in acetonitrile, yielding N-acylpyroglutamic acid without epimerization by way of mixed anhydride formation followed by intramolecular N-acylation.Keywords - angiotensin-converting enzyme; pyroglutamic acid; N-acylpyroglutamic acid; (2S)-1-pyroglutamic acid; N-acetyl-L-pyroglutamic acid
