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Novel design of 3,8-diazabicyclo[3.2.1]octane framework in oxidative sulfonamidation of 1,5-hexadiene

  • 1,5-Hexadiene reacts with trifluoromethanesulfonamide in the oxidative system (t-BuOCl+Nal) to give trans-2,5-bis(iodomethyl)-1-(trifluoromethylsulfonyl)pyrrolidine 5 and 3,8-bis(trifluoromethylsulfonyl)-3,8-diazabicyclo[3.2.1]octane 6. With arenesulfonamides ArSO2NH2 (Ar=Ph, Tol), the reaction stops at the formation of the trans and cis isomers of 2,5-bis(iodomethyl)-1-(arenesulfonyl)pyrrolidine 7 and 8 (1:1). The cis isomers of 7 and 8 do not undergo cyclization to the corresponding 3,8-disubstituted 3,8-diazabicyclo[3.2.1]octanes. The reaction with triflamide represents the first example of one-pot two-step route to 3,8-diazabicyclo[3.2.1]octane system. (C) 2014 Elsevier Ltd. All rights reserved.

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Author:Bagrat A. Shainyan, Mikhail Yu Moskalik, Vera V. Astakhova, Uwe SchildeORCiDGND
ISSN:0040-4020 (print)
Parent Title (English):Tetrahedron
Place of publication:Oxford
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Tag:1,5-Dienes; 3,8-Diazabicyclo[3.2.1]octane; Arenesulfonamides; Cycloaddition; Trifluoromethanesulfonamide; X-ray
First Page:4547
Last Page:4551
Funder:Russian Foundation for Basic Research; Deutsche Forschungsgemeinschaft [RFBR 13-03-00055, RFBR-DFG 11-03-91334]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert