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

作者：Shainyan Bagrat A^*; Moskalik Mikhail Yu; Astakhova Vera V; Schilde Uwe

来源：Tetrahedron, 2014, 70(30): 4547-4551.

DOI：10.1016/j.tet.2014.04.095

• Trifluoromethanesulfonamide
• Arenesulfonamides
• 1,5-Dienes
• Cycloaddition
• 3,8-Diazabicyclo[3.2.1]octane
• X-ray

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.

• 出版日期2014-7-29