Citation: Hui Min Sun, Zhao Peng Liu, Long Qian Tang. Synthesis of novel chiral fluorinating agents, (+)-and (-)-N-fluoro-3-methyl-3-(4-methylphenyl)-2H-benzo [e] [1,2] thiazine-1,1,4-triones[J]. Chinese Chemical Letters, ;2008, 19(8): 907-910. doi: 10.1016/j.cclet.2008.05.036 shu

Synthesis of novel chiral fluorinating agents, (+)-and (-)-N-fluoro-3-methyl-3-(4-methylphenyl)-2H-benzo [e] [1,2] thiazine-1,1,4-triones

a National Institute for the Control of Pharmaceutical and Biological Products, Beijing 100050, China;
b Department of Organic Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China

Received Date: 26 February 2008

Treatment of N-t-butylbenzenesulfonamide with an excess of BuLi, followed by the reaction with methyl 2-(4-methylphenyl)propanoate, gave the corresponding 2-carboxybenzenesulfonamide, which underwent a sequence of consecutive N-deprotective cyclization process mediated by TMSCl-NaI-MeCN reagent to afford the N-sulfonylimine.Following the bromination and ring expansion, 3-methyl-3-(4-methylphenyl)-2H-benzo[e][1,2]thiazine-1,1,4-trione was obtained.Optical resolution of the racemic benzosultam using (-)-menthoxyacetyl chloride, furnished the optically pure (+)-and (-)-3-methyl-3-(4-methylphenyl)-2H-benzo[e][1,2]thiazine-1,1,4-triones, which were fluorinated with FClO₃ to produce the corresponding chiral N-F agents.
- Benzosultams,
- Cyclization,
- TMSCl/NaI/MeCN,
- Enantioselective electrophilic fluorinating agent,
- Chirality
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