TY  - JOUR
A1  - Shainyan, Bagrat A.
A1  - Moskalik, Mikhail Yu
A1  - Astakhova, Vera V.
A1  - Schilde, Uwe
T1  - Novel design of 3,8-diazabicyclo[3.2.1]octane framework in oxidative sulfonamidation of 1,5-hexadiene
JF  - Tetrahedron
N2  - 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.
KW  - Trifluoromethanesulfonamide
KW  - Arenesulfonamides
KW  - 1,5-Dienes
KW  - Cycloaddition
KW  - 3,8-Diazabicyclo[3.2.1]octane
KW  - X-ray
Y1  - 2014
U6  - https://doi.org/10.1016/j.tet.2014.04.095
SN  - 0040-4020
VL  - 70
IS  - 30
SP  - 4547
EP  - 4551
PB  - Elsevier
CY  - Oxford
ER  -