STEREOCHEMISTRY OF THE ADDITION OF ALPHA-METALATED N,N-DIMETHYLSULFONAMIDES TO 4-TERT-BUTYLCYCLOHEXANONE

The effects of some reaction conditions on the aldol reaction of RCH(M)S02N(CH,)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 = MgCI and M = Li, while M = Na gives 100% axial attack. These, and several more observations cannot be interpreted in terms of current concepts of nucleophilic additions to 4-t-butylcyclohexanone. © 1990, Taylor & Francis Group, LLC. All rights reserved.