Sequential double α-arylation of N-allylureas by asymmetric deprotonation and N→C aryl migration.
On lithiation with lithium amides, N-allyl-N'-aryl ureas undergo rearrangement with transfer of the aryl ring from N to the allylic α carbon. From the α-arylated products, a further aryl transfer under the influence of a chiral lithium amide allows the enantioselective construction of 1,1-diarylallylamine derivatives. Stereoselectivity in these reactions results from the enantioselective formation of a planar chiral allyllithium under kinetic control.
School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Daniel J
DJ
Tetlow
Ulrich
U
Hennecke
James
J
Raftery
Michael J
MJ
Waring
David S
DS
Clarke
Jonathan
J
Clayden
D002244:Carbon / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
C095407:2-propenylurea; D002244:Carbon; D014508:Urea; D009584:Nitrogen