128622-76-4Relevant articles and documents
STEREOCHEMISTRY OF THE ADDITION OF α-METALLATED N,N-DIMETHYLSULFONAMIDES TO 4-t-BUTYLCYCLOHEXANONE
Mladenova, Margarita,Gaudemar-Bardone, Francoise
, p. 191 - 197 (2007/10/02)
The effects of some reaction conditions on the aldol reaction of RCH(M)SO2N(CH3)2 and product stereochemistries are reported.Under thermodynamic control the reaction is nonstereoselective.Under kinetic control, stereoselectivity varies with R.For R = H, axial attack is slightly favoured, while equatorial attack is dominant for R = CH3.Dimethyl phenylmethanesulfonamide reacts highly stereoselectively.Equatorial attack is favoured with M = MgCl and M = Li, while M = Na gives 100percent axial attack.These, and several more observations cannot be interpreted in terms of current concepts of nucleophilic additions to 4-t-butylcyclohexanone.