Synthesis of optically active 1-fluoroalkyl benzenes

作者: Elke Fritz-Langhals

DOI: 10.1016/S0040-4039(00)73178-9

关键词: FluorideOptically activeCaesiumPolar effectOrganic chemistryChemistryPolymer chemistryNucleophilic substitution

摘要: Abstract A simple synthesis of optically active 1-fluoroalkyl benzenes bearing electron withdrawing substituents is developed. Optically 1-hydroxyalkyl are converted into the methanesulfonates and subsequently 1 by use fluorinating agent cesium fluoride/N-methyl-formamide.

参考文章(16)
John T. Welch, Tetrahedron report number 221 Tetrahedron. ,vol. 43, pp. 3123- 3197 ,(1987) , 10.1016/S0040-4020(01)90286-8
Yun. Gao, K. Barry. Sharpless, Vicinal diol cyclic sulfates. Like epoxides only more reactive Journal of the American Chemical Society. ,vol. 110, pp. 7538- 7539 ,(1988) , 10.1021/JA00230A045
Ronald K. Crossland, Kenneth L. Servis, Facile synthesis of methanesulfonate esters Journal of Organic Chemistry. ,vol. 35, pp. 3195- 3196 ,(1970) , 10.1021/JO00834A087
John A. Wilkinson, Recent advances in the selective formation of the carbon-fluorine bond Chemical Reviews. ,vol. 92, pp. 505- 519 ,(1992) , 10.1021/CR00012A002
Elke Fritz-Langhals, Gabi Schu¨tz, Simple synthesis of optically active 2-fluoropropanoic acid and analogs of high enantiomeric purity Tetrahedron Letters. ,vol. 34, pp. 293- 296 ,(1993) , 10.1016/S0040-4039(00)60570-1
Kazuhiko Sakaguchi, Yutaka Shiomi, Mitsuhlro Koden, Tomoaki Kuratate, Chiral γ-lactones for FLC. The relationship between the molecular structures and the properties Ferroelectrics. ,vol. 121, pp. 205- 211 ,(1991) , 10.1080/00150199108217624
R.W. Feenstra, E.H.M. Stokkingreef, R.J.F. Nivard, H.C.J. Ottenheijm, Interconversion of (R) and (S)-α-hydroxy esters: precursors of (S) and (R)-o-benzyl-α-hydroxylamino acid esters of high optical purity Tetrahedron. ,vol. 44, pp. 5583- 5595 ,(1988) , 10.1016/S0040-4020(01)86063-4
Sei'Ichi Arakawa, Kei'Ichi Nito, Jun'Etsu Seto, Synthesis of Fluorine-Containing Ferroelectric Liquid Crystals Molecular Crystals and Liquid Crystals. ,vol. 204, pp. 15- 25 ,(1991) , 10.1080/00268949108046590
Tadahiko Tsushima, Kenji Kawada, Teruji Tsuji, Katsuya Tawara, Fluorine-containing amino acids and their derivatives. 4. Synthesis and antibacterial activity of threo and erythro 1-fluorodehydroxylated chloramphenicol analogues. Journal of Medicinal Chemistry. ,vol. 28, pp. 253- 256 ,(1985) , 10.1021/JM00380A019
R. Bohlmann, Fluor in der organischen Synthese Nachrichten aus Chemie, Technik und Laboratorium. ,vol. 38, pp. 40- 43 ,(1990) , 10.1002/NADC.19900380112