TY - JOUR
T1 - Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation
AU - Pandiancherri, Shveta
AU - Lupton, David W
PY - 2011
Y1 - 2011
N2 - Exposure of N-chloroamines to (KOBu)-Bu-t or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of pi 4s + pi 2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. (C) 2010 Published by Elsevier Ltd.
AB - Exposure of N-chloroamines to (KOBu)-Bu-t or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of pi 4s + pi 2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines. (C) 2010 Published by Elsevier Ltd.
UR - http://www.sciencedirect.com.ezproxy.lib.monash.edu.au/science?_ob=MImg&_imagekey=B6THS-51M0N6F-9-3D&_cdi=5290&_user=542840&_pii=S0040403910021751&_or
U2 - 10.1016/j.tetlet.2010.11.142
DO - 10.1016/j.tetlet.2010.11.142
M3 - Article
VL - 52
SP - 671
EP - 674
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 6
ER -