91084-05-8Relevant articles and documents
Urethanes synthesis from oxamic acids under electrochemical conditions
Ogbu, Ikechukwu Martin,Lusseau, Jonathan,Kurtay, Gülbin,Robert, Frédéric,Landais, Yannick
supporting information, p. 12226 - 12229 (2020/10/26)
Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.
1,2-Dimethoxy-4,5-dimethylene: A new protecting group for acyclic amino acid derivatives prepared by Stevens rearrangement
Tayama, Eiji,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
, p. 1373 - 1375 (2012/03/27)
A new protecting group, 1,2-dimethoxy-4,5-dimethylene, for acyclic amino acid derivatives could be introduced by N,N-dialkylation with 1,2-bis(bromomethyl)-4,5-dimethoxybenzene (1) and removed via amine de-alkylation with acyl chlorides. The method can be used with base-induced [2,3] and [1,2] Stevens rearrangement products.
Practical synthesis of fluorous oxazolidinone chiral auxiliaries from α-amino acids
Hein, Jason E.,Geary, Laina M.,Jaworski, Ashley A.,Hultin, Philip G.
, p. 9940 - 9946 (2007/10/03)
A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral α-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.