163084-89-7Relevant articles and documents
Synthesis of Unnatural α-Amino Acid Derivatives via Light-Mediated Radical Decarboxylative Processes
Merkens, Kay,Aguilar Troyano, Francisco José,Djossou, Jonas,Gómez-Suárez, Adrián
, p. 2354 - 2359 (2020)
Unnatural amino acids (UAAs) are key building blocks with widespread application across several scientific fields. Therefore, it is highly attractive to develop straightforward and simple methodologies capable of granting quick access to these species. Herein we report a light-mediated protocol for the synthesis of UAA via radical decarboxylative processes. This methodology, which employs readily available and abundant starting materials – such as carboxylic and α-keto acids – proceeds under very mild reaction conditions and shows a high functional group tolerance. In addition, the products of the radical reaction can be readily derivatized to grant rapid access to complex UAAs. (Figure presented.).
Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach
Dong, Yue,Huang, He,Ji, Peng,Wang, Wei,Wei, Yongyi,Zhang, Yueteng
, (2020)
A mild, versatile organophotoredox protocol has been developed for the preparation of diverse, enantioenriched α-deuterated α-amino acids. Distinct from the well-established two-electron transformations, this radical-based strategy offers the unrivaled ca
Decarboxylative Radical Addition to Methylideneoxazolidinones for Stereocontrolled Synthesis of Selectively Protected Diamino Diacids
Annadate, Ritesh,Beadle, Jonathan,Hsiao, Yu-Ting,Pascoe, Cameron,Vederas, John C.
, p. 7270 - 7273 (2021/10/01)
Syntheses of stereochemically pure and selectively protected diamino diacids can be achieved by redox decarboxylation of distal N-hydroxyphthalimide esters of protected aspartic, glutamic or α-aminoadipic acids via radical addition to methylideneoxazolidinones. The products are useful for solid-supported syntheses of robust bioactive carbocyclic peptide analogs. Yields of reactive primary radical addition are superior to those of more stabilized radicals, and the reaction fails if the alkylideneoxazolidinone has a methyl substituent on its terminus (i.e., 13a/13b).