Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N'-diarylureas and diaryl ethers: advantages of a relay axis.
The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N'-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95 : 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.
Betson
Mark S
MS
School of Chemistry, University of Manchester, Oxford Road, Manchester, UKM13 9PL.
Bracegirdle
Ann
A
Clayden
Jonathan
J
Helliwell
Madeleine
M
Lund
Andrew
A
Pickworth
Mark
M
Snape
Timothy J
TJ
Worrall
Christopher P
CP
D004987:Ethers / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009930:Organic Chemicals / Q000138:chemical synthesis / Q000737:chemistry; D014508:Urea / Q000737:chemistry
D004987:Ethers; D006841:Hydrocarbons, Aromatic; D009930:Organic Chemicals; D014508:Urea