TY - JOUR
T1 - Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism
AU - Branco, Paula Cristina de Sério
AU - Bonifácio, Vasco
AU - Lobo, Ana Maria Félix Trindade
AU - Prabhakar, Alberto Sundaresan
PY - 2007/1/1
Y1 - 2007/1/1
N2 - The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins were selected to study the stereochemistry of the reaction. A Pd(IV) intermediate is proposed as the aziridinating species.
AB - The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins were selected to study the stereochemistry of the reaction. A Pd(IV) intermediate is proposed as the aziridinating species.
U2 - 10.1016/j.tet.2007.05.020
DO - 10.1016/j.tet.2007.05.020
M3 - Article
SN - 0040-4020
VL - 63
SP - 7009
EP - 7017
JO - Tetrahedron
JF - Tetrahedron
IS - 30
ER -