Relaying stereochemistry through aromatic ureas: 1,9 and 1,15 remote stereocontrol.
The well-defined conformation of an N,N'-diarylurea allows a chiral sulfinyl substituent to influence diastereoselectivity in the formation of new stereogenic centres up to 14 bond lengths away.
Clayden
Jonathan
J
School of Chemistry, University of Manchester, Oxford Road, Manchester, UK M13 9PL. Clayden@man.ac.uk
Pickworth
Mark
M
Jones
Lyn H
LH
D018360:Crystallography, X-Ray; D008956:Models, Chemical; D008968:Molecular Conformation; D013237:Stereoisomerism; D013696:Temperature; D014508:Urea / Q000737:chemistry*
D014508:Urea