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.
| Author details: | Bagrat A. Shainyan, Mikhail Yu Moskalik, Vera V. Astakhova, Uwe SchildeORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1016/j.tet.2014.04.095 |
| ISSN: | 0040-4020 |
| Title of parent work (English): | Tetrahedron |
| Publisher: | Elsevier |
| Place of publishing: | Oxford |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2014 |
| Publication year: | 2014 |
| Release date: | 2017/03/27 |
| Tag: | 1,5-Dienes; 3,8-Diazabicyclo[3.2.1]octane; Arenesulfonamides; Cycloaddition; Trifluoromethanesulfonamide; X-ray |
| Volume: | 70 |
| Issue: | 30 |
| Number of pages: | 5 |
| First page: | 4547 |
| Last Page: | 4551 |
| Funding institution: | 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 |
