A practical route for the highly stereoselective synthesis of tetrasubstituted fluoroalkenes

被引:16
作者
Cao, Chun-Ru [1 ]
Ou, Song [1 ]
Jiang, Min [1 ]
Liu, Jin-Tao [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGH-YIELD SYNTHESIS; JULIA OLEFINATION; WEINREB AMIDES; FLUORO; PHARMACEUTICALS; EFFICIENT; SULFONES; ALKENES; ESTERS; MILD;
D O I
10.1039/c3ob42093k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of tetrasubstituted fluoroatkene derivatives were synthesized by the reaction of alpha-fluoro-beta-carbonyl benzothiazol-2-yl sulfones with various nucleophiles in good yields with high stereoselectivities. The predominant cis configuration of fluorine and alkynyl groups was observed. A single isomer was obtained when a ketone, acetate or amide was used as the substrate in the presence of a base.
引用
收藏
页码:467 / 473
页数:7
相关论文
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[41]   1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia-Kocienski olefination [J].
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