Exopericyclic stereocontrol in Johnson-Claisen rearrangements of allylic sulfides.
A study of the effects of exopericyclic stereocentres on the stereoselectivity of Johnson-Claisen rearrangements of thioether-containing allylic alcohols shows that selectivity is highly dependent upon allylic substitution patterns.
Craig
Donald
D
Department of Chemistry, Imperial College London, South Kensington Campus, London, SW7 2AZ, UK. d.craig@imperial.ac.uk
Harvey
John W
JW
O'Brien
Alexander G
AG
White
Andrew J P
AJ
D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry*
D000498:Allyl Compounds; D004952:Esters; D013438:Sulfhydryl Compounds; D013440:Sulfides