6310-42-5Relevant 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
supporting information, p. 2354 - 2359 (2020/05/06)
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.).
A highly diastereoselective decarboxylative mannich reaction of β-keto acids with optically active N-sulfinyl α-imino esters
Yang, Cui-Feng,Shen, Chen,Wang, Jian-Yong,Tian, Shi-Kai
supporting information; experimental part, p. 3092 - 3095 (2012/08/28)
A range of protected γ-oxo-α-amino esters have been prepared in a highly regio- and stereoselective manner through the decarboxylative Mannich reaction of β-keto acids with optically active N-tert-butanesulfinyl α-imino esters in the presence of 3 mol % La(OTf)3 or 5 mol % Y(OTf)3 at 20 °C. Preliminary mechanistic studies indicate that the reaction proceeds through imine addition followed by decarboxylation.
Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids
Barfoot, Christopher W.,Harvey, Joanne E.,Kenworthy, Martin N.,Kilburn, John Paul,Ahmed, Mahmood,Taylor, Richard J.K.
, p. 3403 - 3417 (2007/10/03)
Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues.
