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  - 
TY  - JOUR
A1  - Moskalik, Mikhail Yu.
A1  - Astakhova, Vera V.
A1  - Schilde, Uwe
A1  - Sterkhova, Irina V.
A1  - Shainyan, Bagrat A.
T1  - Assembling of 3,6-diazabicyclo[3.1.0]hexane framework in oxidative triflamidation of substituted buta-1,3-dienes
JF  - Tetrahedron
KW  - Trifluoromethanesulfonamide
KW  - Arenesulfonamides
KW  - Cycloaddition
KW  - 1,3-Dienes
KW  - 3,6-Diazabicyclo[3.1.0]hexanes
KW  - X-ray
Y1  - 2014
U6  - https://doi.org/10.1016/j.tet.2014.09.050
SN  - 0040-4020
VL  - 70
IS  - 45
SP  - 8636
EP  - 8641
PB  - Elsevier
CY  - Oxford
ER  - 
TY  - JOUR
A1  - Wessig, Pablo
A1  - Pick, Charlotte
A1  - Schilde, Uwe
T1  - First example of an atropselective dehydro-Diels-Alder (ADDA) reaction
JF  - Tetrahedron letters
N2  - A new concept of a stereoselective synthesis of axially chiral biaryls, formed in the course of the dehydro-Diels-Alder (DDA) reaction, has been disclosed. It is based on asymmetric induction of the newly formed chirality axis by a chirality center, which is present in the two synthesized DDA reactants. Depending on the different length of the linkers joining the alkyne moieties the DDA reaction may be triggered photochemically or thermally, where only the thermal variant was stereoselective.
KW  - Cycloaddition
KW  - Atropselecrivity
KW  - Biaryls
KW  - Alkynes
KW  - Photochemistry
Y1  - 2011
U6  - https://doi.org/10.1016/j.tetlet.2011.06.024
SN  - 0040-4039
VL  - 52
IS  - 32
SP  - 4221
EP  - 4223
PB  - Elsevier
CY  - Oxford
ER  -