ChemInform Abstract: Preparation of trans‐2‐Substituted‐4‐halopiperidines and cis‐2‐Substituted‐4‐halotetrahydropyrans via AlCl3‐Catalyzed Prins Reaction. Issue 44 (13th October 2016)

• Record Type: Journal Article
• Authors: Liu, Gong‐Qing; Cui, Bin; Xu, Rong; Li, Yue‐Ming
• Is Part Of: ChemInform. Volume 47:Issue 44(2016)
• Page Start: no
• Page End: no
• Publication Date: 2016-10-13
• Subjects: cascade reactions, domino reactions, tandem reactions -- halogenation -- ring closure reactions, annulation reactions -- catalysis, phase‐transfer catalysis -- diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism); Chemistry -- Abstracts -- Periodicals; 540.5
• DOI: 10.1002/chin.201644057
• Languages: English
• ISSNs: 0931-7597

Abstract

Abstract: Whereas the title reaction between N‐tosyl homoallylamine with aryl or alkyl aldehydes and trimethylsilyl bromide, chloride or iodide delivers the corresponding 2‐substituted 4‐halopiperidines with high trans selectivity, application of trimethylsilyl fluoride provides mixtures of cis and trans isomers.