956264-72-5Relevant academic research and scientific papers
Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi's Catalyst
Sasano, Yusuke,Sato, Hikaru,Tadokoro, Shinsuke,Kozawa, Masami,Iwabuchi, Yoshiharu
, p. 571 - 577 (2019/03/19)
A method for safe and scalable aerobic alcohol oxidation using 2-azaadamantan-2-ol (AZADOL), an azaadamantane-type hydroxylamine catalyst, with a NOx cocatalyst in a conventional batch reactor has been developed. The use of 2 mol % AZADOL and 10 mol % NaNO2 was determined to promote aerobic alcohol oxidation quantitatively within a reasonable time (8 h). Safety is ensured by controlling the reaction temperature below the flash point of the acetic acid solvent. The robustness of the developed method is demonstrated by the 500 g scale oxidation of diacetone fructose into Shi's catalyst for asymmetric epoxidation.
Chemoenzymatic synthesis of idesolide from benzoic acid
Adams, David R.,Aichinger, Christian,Rinner, Uwe,Hudlicky, Tomas
, p. 725 - 729 (2011/04/26)
Idesolide was synthesized in five steps from benzoic acid by base-catalyzed dimerization of hydroxy keto ester, obtained from diol, the product of the whole-cell fermentation of benzoic acid with R. eutrophus B9. Georg Thieme Verlag Stuttgart - New York.
Highly efficient, organocatalytic aerobic alcohol oxidation
Shibuya, Masatoshi,Osada, Yuji,Sasano, Yusuke,Tomizawa, Masaki,Iwabuchi, Yoshiharu
supporting information; experimental part, p. 6497 - 6500 (2011/06/23)
5-Fluoro-2-azaadamantane N-oxyl (5-F-AZADO) realizes a simple, organocatalytic aerobic alcohol oxidation system that has a wide scope under mild conditions at ambient pressure and temperature and is weakly acidic and halogen- and transition-metal-free. The oxoammonium nitrate (5-F-AZADO +NO3-) works as a bifunctional catalyst of 5-F-AZADO and NOx that enables the catalytic aerobic oxidation of alcohols by itself (a metal-salt-free system).
Enantioselective total synthesis of idesolide via NaHCO3- promoted dimerization
Nagasawa, Tomohiro,Shimada, Naoyuki,Torihata, Munefumi,Kuwahara, Shigefumi
experimental part, p. 4965 - 4969 (2010/08/19)
The enantioselective total synthesis of idesolide has been accomplished in 20% overall yield from a known allylic alcohol by a nine-step sequence involving the Sharpless asymmetric epoxidation as the source of chirality and an efficient NaHCO3-promoted dimerization of the monomeric form of idesolide as the key transformation.
Total synthesis and determination of the absolute configuration of (-)-idesolide
Yamakoshi, Hiroyuki,Shibuya, Masatoshi,Tomizawa, Masaki,Osada, Yuji,Kanoh, Naoki,Iwabuchi, Yoshiharu
supporting information; experimental part, p. 980 - 983 (2010/06/15)
(Chemical Equetion Presentation) The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)4-Bn-1-Bu-AZADO- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-
