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Difluoromethyl 2-Pyridyl Sulfoximine:A Stereoselective Nucleophilic Reagent for Difluoro(aminosulfinyl)methylation and Difluoro(aminosulfonyl)methylation
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作者 Qinghe Liu Chuanfa Ni +2 位作者 Qian Wang depei meng Jinbo Hu 《CCS Chemistry》 CAS 2022年第11期3648-3659,共12页
1,1-Difluorinated sulfonamides are known to have better anti-inflammatory activity and enzyme inhibitory potency than their nonfluorinated counterparts.Two geminal fluorine atoms cause electronic perturbation of the n... 1,1-Difluorinated sulfonamides are known to have better anti-inflammatory activity and enzyme inhibitory potency than their nonfluorinated counterparts.Two geminal fluorine atoms cause electronic perturbation of the nearby polar groups enhanced the biological activity of the 1,1-difluorinated sulfonamides.However,because methods for their stereoselective synthesis are scarce,such entities remain entirely unexplored.Here,we outline an efficient method for the stereoselective introduction of the difluoro(aminosulfonyl)methyl group(CF_(2)SO_(2)NH_(2))into carbonyls,imines,and alkyl halides with a new(R)-2-pyridyl difluoromethyl sulfoximine reagent,which provides a unique solution for the synthesis of chiralα,α-difluorinated sulfonamides with a quaternary stereocenter.Its potency is illustrated by the synthesis of fluorinated analogues of bioactive compounds such as 2-OH-SA,an antagonist for the GABA_(B)receptor in guinea pig ileum,and the late-stage modification of complex molecules such as haloperidol,ebastine,cholesterol,and(+)-δ-tocopherol derivatives.Stereoselective difluoro(aminosulfinyl)methylation to yield chiral sulfinylamides is presented,showcasing other uses of this new reagent. 展开更多
关键词 difluoro(aminosulfonyl)methylation difluoro(aminosulfinyl)methylation STEREOSELECTIVE NUCLEOPHILIC SULFOXIMINE
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