- Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
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Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
- Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
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- An aryne-based three-component access to α-aroylamino amides
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Aryne chemistry has recently received widespread attention and isocyanides have been reported as efficient nucleophilic partners in a set of multicomponent transformations. In this study, we demonstrate that tertiary α-monosubstituted α-isocyanoacetamides are efficaciously coupled with water and benzyne to offer a direct and metal-free access to densely functionalized α-benzoylamino amides, without competing with the intramolecular cyclization to 5-aminooxazoles. Despite the formation of the aryl anion as a key intermediate, the reaction displays a stereoconservative course, allowing for the preparation of enantiomerically pure α-benzoylamino amides. Finally, the synthetic utility of the reported MCR was exemplified by the preparation of proglumide, a cholecystokinin antagonist.
- Serafini, Marta,Griglio, Alessia,Viarengo, Sara,Aprile, Silvio,Pirali, Tracey
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p. 6604 - 6612
(2017/08/16)
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- New glutamic and aspartic derivatives with potent CCK-antagonistic activity
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New derivatives of aspartic and glutamic acid were synthesized and evaluated in vitro and in vivo for anti-CCK activity on the guinea pig gallbladder. The anti-CCK activity of some 4-benzamido-glutaramic acid derivatives was a hundred times greater than that of proglutamide, the model compound, and they have been selected for further studies.
- Makovec,Chiste,Bani,et al.
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