88790-04-9Relevant academic research and scientific papers
Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides accompanying with [1,2]-rearrangement of the acyloxy group and anodic cyclization of 2-(t-butoxycarbonyl)oxy-3,3,3-trifluoropropyl sulfide
Isokawa, Motoaki,Sano, Masaru,Kubota, Kiyotaka,Suzuki, Katsutoshi,Inagi, Shinsuke,Fuchigami, Toshio
, p. G121 - G127 (2017/11/17)
Anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides was carried out in methanol containing Et3N-3HF as a supporting electrolyte and mediator using an undivided cell to provide the corresponding α-methoxylated products and unexpecte
Highly stereocontrolled access to 1,1,1-trifluoro-2,3-epoxypropane via lipase-mediated kinetic resolution of 1,1,1-trifluoro-3-(phenylthio)propan-2-ol and its application
Shimizu, Makoto,Sugiyama, Kouki,Fujisawa, Tamotsu
, p. 2655 - 2659 (2007/10/03)
1,1,1-Trifluoro-3-(phenylthio)propan-2-ol was prepared in high enantiomeric purity by lipase-mediated kinetic resolution of the corresponding esters. The resolved alcohol was successfully converted into 1,1,1 -trifluoro-2,3-epoxypropane and/or used in the
Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent
Linderman, Russell J.,Graves, David M.
, p. 661 - 668 (2007/10/02)
The efficient oxidation of mono-, di-, tri-, and perfluoroalkyl-substituted carbinols has been accommplished by the Dess-Martin periodinane oxidant.A variety of functional groups are compatible with the oxidation procedure.Monitoring the oxidation by 19F NMR indicated that a discreet periodinane intermediate is formed during the course of the reaction.Nonnucleophilic or sterically encumbered α-thiofluoro carbinols were readily oxidized; however, a nucleophilic α-thio-substituted trifluoromethyl carbinol was not.A tert-butyl alcohol modified periodinane oxidant was ultimately employed to achieve oxidation in this example.
2-HALOVINYL ARYL SULFONES: NEW COUPLING REAGENTS FOR CARBOXAMIDE FORMATION
Shimagaki, Masayuki,Koshiji, Hiroko,Oishi, Takeshi
, p. 45 - 58 (2007/10/02)
E-2-Chlorovinyl p-nitrophenyl sulfone 6 and 2-bromo-2-trifluoromethylvinyl phenyl sulfone 7a reacted with carboxylic acids in the presence of a molar equiv of Et3N affording the corresponding 2-acyloxyvinyl sulfones 8, 11, 17, 18, 22, 25, 28 and 29.The latter, on treatment with amines, gave amides 9, 13, 19, 23 and 26 and peptides 30 and 32.These reagents 6 and 7a were also used for the formation of N-methylanilides 13d, 13e, 19d, 23 and 26.Particularly, 6 was successfully used for synthesis of a macrocyclic lactam 23 involving a N-methylanilide moiety.The amidation reac tions proceeded under essentially neutral conditions.Therefore, base-sensitive β-hydroxycarboxy-N-methylanilides such as 26, whose structural unit was involved in maytansine 5, could be prepared by the present method.The reagent 6 was also effective for the preparation of peptides such as Val-N-MeVal derivatives (e.g.32), which were difficult to prepare by other methods.
