91174-01-5Relevant articles and documents
N-Chloro- N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light
Jeon, Hyun Ji,Lee, Wongyu,Seo, Sangwon,Chang, Sukbok
supporting information, p. 1176 - 1183 (2021/05/31)
Herein, we describe the scalability and sustainability investigations toward the visible light-mediated amidation of aldehydes with N-chloro-N-sodio-carbamates. The practicality credentials of N-chloro-N-sodio-carbamates for their use in multigram scale a
Total synthesis of (-)-ephedradine A: An efficient construction of optically active dihydrobenzofuran-ring via C-H insertion reaction
Kurosawa, Wataru,Kobayashi, Hideki,Kan, Toshiyuki,Fukuyama, Tohru
, p. 9615 - 9628 (2007/10/03)
The stereocontrolled total synthesis of (-)-ephedradine A (1) has been accomplished. Construction of optically active dihydrobenzofuran-ring was performed by a novel asymmetric C-H insertion reaction. After an intramolecular ester-amide exchange reaction and a Sharpless asymmetric aminohydroxylation reaction, construction of the complex macrocyclic ring was performed by Ns-strategy and an intramolecular aza-Wittig reaction. Graphical Abstract.
Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran
Haukaas, Michael H.,O'Doherty, George A.
, p. 401 - 404 (2007/10/03)
(Equation Presented) The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing β-hydroxyfurfurylamine 5a with enantioexcess of >86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The key steps include the use of an aza-Achmatowicz reaction, a diastereoselective Luche reduction, diastereoselective dihydroxylation, and a tandem Cbz deprotection/reductive amination.