850148-82-2Relevant academic research and scientific papers
New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines
Lencina, Claiton Leoneti,Dassonville-Klimpt, Alexandra,Sonnet, Pascal
, p. 1689 - 1697 (2008/12/21)
The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously descri
Simple, versatile and highly diastereoselective synthesis of 1,3,4-trisubstituted-2-oxopiperazine-containing peptidomimetic precursors
Franceschini, Nicolas,Sonnet, Pascal,Guillaume, Dominique
, p. 787 - 793 (2007/10/03)
The selective O-deprotection of (1'S)-4-(tert-butoxycarbonyl)-1-[1'- phenylmethyloxymethyl-2'-[(tert-butyldimethylsilyl)oxy]ethyl]-2-oxopiperazine furnished an enantiomerically pure alcohol whose regio- and diastereoselective C3-alkylation yielded either (3R)- or (3S)-1,3,4-trisubstituted-2- oxopiperazines in high diastereomeric purity. These derivatives were efficiently transformed into (1'A)- or (1'S)-peptide templates utilizable to prepare peptidomimetics. This method provides easy access to each 1,3,4-trisubstituted- 2-oxopiperazine diastereomer and facilitates, through the large choice of substituents at the 3-position together with the chemistry that can be performed on the NI substituent, the preparation of a large number of diastereomerically pure constrained peptidomimetics from a single precursor. The Royal Society of Chemistry 2005.
