96133-49-2Relevant academic research and scientific papers
Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators
Wang, Fei,Rafiee, Mohammad,Stahl, Shannon S.
supporting information, p. 6686 - 6690 (2018/05/07)
An electrochemical method has been developed for α-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1 V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate oxidation. This reaction also represents the first α-functionalization of non-activated cyclic carbamates with oxoammonium oxidants.
Electroorganic Chemistry. Part 80. α-Hydroxylation of N-Acylated Cyclic Amines and Utilization of the Products as Amino Aldehyde Equivalents
Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu,Habuka, Masahiro,Uchida, Kenshi,Toyoda, Katsuya
, p. 2876 - 2889 (2007/10/02)
A general method for the transformation of N-acylated cyclic amines (1) to amino aldehydes (4) was exploited.N-Benzoyl- or N-alkoxycarbonyl-α-methoxyamines (2) were prepared by anodic reaction of (1) in methanol.Treatment of (2) with dilute hydrochloric acid gave the corresponding α-hydroxylated compounds (3) which are amino aldehydes equivalents.The reaction of (3) with methoxycarbonylmethylenetriphenylphosphorane yielded ω-amino-α,β-unsaturated esters in satisfactory yields.
