106372-59-2Relevant articles and documents
Reactive resin facilitated preparation of an enantiopure fluorobicycloketone
Wong, Audrey,Welch, Christopher J.,Kuethe, Jeffrey T.,Vazquez, Enrique,Shaimi, Mohamed,Henderson, Derek,Davies, Ian W.,Hughes, David L.
, p. 168 - 174 (2004)
A facile preparation of enantiopure ethyl (1S,SS,6S)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate 1 is described. The key feature of the synthesis involves copper-catalyzed enantioselective intramolecular cyclopropanation of a diazoketone to form enado-fluorocyclopropane 1 in a single operation. Removal of a problematic chloroketone impurity using a reactive resin treatment enabled a high throughput enantiopurity upgrade by chiral HPLC. The development of a scalable synthesis of 1 is presented, including details of the selection of catalyst and ligand optimization, incorporation of a reactive resin treatment and selection of chiral HPLC media and conditions.
Anodic fluorination based on cation exchange between alkali-metal fluorides and solid-supported acids
Tajima, Toshiki,Nakajima, Atsushi,Doi, Yuta,Fuchigami, Toshio
, p. 3550 - 3552 (2007)
(Chemical Equation Presented) Positively shocking: The interchange of cations between alkali-metal fluorides and solid-supported acids (see picture) in an electrolytic system promotes the anodic fluorination of organic compounds to give the corresponding
Highly selective electrochemical fluorination of dithioacetal derivatives bearing electron-withdrawing substituents at the position α to the sulfur atom using poly(HF) salts
Yin, Bin,Inagi, Shinsuke,Fuchigami, Toshio
supporting information, p. 85 - 91 (2015/02/05)
Anodic fluorination of dithioacetals bearing electron-withdrawing ester, acetyl, amide, and nitrile groups at their α-positions was comparatively studied using various supporting poly(HF) salts like Et3N·nHF (n = 3-5) and Et4NF·nHF (
Scandium-catalyzed carbon-carbon bond formations using α- organosulfanyl and organoselanyl-α-fluoroacetic acid derivatives
Gotoh, Kohei,Yamamoto, Teruhisa,Yoshimatsu, Mitsuhiro
, p. 1611 - 1615 (2007/10/03)
The scandium-catalyzed reactions of α-organosulfanyl and organoselanyl-α-fluoroacetates 1-2, acetamides 3-4 and acetonitrile 5 with soft nucleophiles proceeded to give the products 6a-b, 7a-c, 8a-c, 9a-e in good to high yields. We also successfully perfor
