Novel enantioselective fluorinating agents, (R)- and (S)-N-fluoro-3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides.
Enantioselective fluorinating agents, (R)- and (S)-,N-fluoro-3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides (BNBT-F, 2) are readily prepared in 3 steps from racemic 3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxides (5) via optical resolution and fluorination. These agents make accessible both enantiomers of optically active quaternary alpha-fluoro carbonyl compounds in modest to high enantioselectivities. X-ray crystallographic analysis of chiral 2 reveals a unique structure wherein the nitrogen atom is highly pyramidalized and fluorine occupies an axial position.
Shibata
N
N
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Japan.
Liu
Z
Z
Takeuchi
Y
Y
D018360:Crystallography, X-Ray; D003499:Cyclic S-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D008968:Molecular Conformation; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry
D003499:Cyclic S-Oxides; C423468:N-fluoro-3-tert-butyl-7-nitro-3,4-dihydro-2H-benzo(e)(1,2)thiazine 1,1-dioxide; D013843:Thiazines; D005461:Fluorine