TY - JOUR
T1 - 1,3-dipolar cycloaddition of unstabilised azomethine ylides by lewis base catalysis
AU - Pandiancherri, Shveta
AU - Ryan, Sarah J
AU - Lupton, David
PY - 2012
Y1 - 2012
N2 - Lewis base catalysed 1,3-dipolar cycloaddition between alpha,beta-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol DMAP. Competition experiments and 19F-NMR studies indicate that the cycloaddition occurs preferentially between the alpha,beta-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14 ee.
AB - Lewis base catalysed 1,3-dipolar cycloaddition between alpha,beta-unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol DMAP. Competition experiments and 19F-NMR studies indicate that the cycloaddition occurs preferentially between the alpha,beta-unsaturated acyl fluoride and the unstabilised azomethine ylide. In addition, an enantioselective variant, using chiral isothiourea catalysts, has been achieved with 14 ee.
UR - http://pubs.rsc.org.ezproxy.lib.monash.edu.au/en/content/articlepdf/2012/ob/c2ob26047f?page=search
U2 - 10.1039/c2ob26047f
DO - 10.1039/c2ob26047f
M3 - Article
VL - 10
SP - 7903
EP - 7911
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
SN - 1477-0520
IS - 39
ER -