%0 Journal Article
%A Ventosa-Andrés, Pilar
%A Hradilová, Ludmila
%A Krchňák, Viktor
%D 2014
%T Privileged Structures as Peptide Backbone Constraints:
Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone
Peptides
%U https://acs.figshare.com/articles/journal_contribution/Privileged_Structures_as_Peptide_Backbone_Constraints_Polymer_Supported_Stereoselective_Synthesis_of_Benzimidazolinopiperazinone_Peptides/2274688
%R 10.1021/co500023k.s001
%2 https://acs.figshare.com/ndownloader/files/3910714
%K Conventional
%K functionalized
%K cyclization
%K target compounds
%K synthese
%K acid
%K integrity
%K microwave conditions
%K Privileged Structures
%K acylation
%K synthesis
%K peptide backbone
%K tandem
%K Peptide Backbone Constraints
%K Significant epimerization
%K stereocontrol
%K constraint
%K Stereoselective
%K efficiency
%K stereogenic center
%K Benzimidazolinopiperazinone PeptidesA
%K Synthesi
%K scaffold
%X A molecular
scaffold comprising a privileged structure was designed
and synthesized to serve as a peptide backbone conformational constraint.
The synthesis of highly functionalized 2,3,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-4(1H)-ones on a solid-phase support was performed via a tandem N-acyl-N-aryliminium ion cyclization–nucleophilic
addition reaction. The synthesis proceeded with full stereocontrol
of the newly formed stereogenic center. Conventional and microwave-assisted
syntheses were compared with respect to efficiency and the optical
integrity of the target compounds. Significant epimerization was observed
during acylation with (S)- and (R)-2-bromopropionic acids under microwave conditions.
%I ACS Publications