128622-74-2Relevant academic research and scientific papers
Stereochemistry of the addition of metallated sulfonamides to substituted cyclohexanones
Stanchev,Stephan,Christov,Rumen,Simova,Svetlana,Mladenova,Margarita,Linden,Anthony
, p. 123 - 134 (2007/10/03)
The addition of α-metallated sulfonamides to cyclic ketones has been studied.Under kinetic control the axial attack of the lithium and the cerium reagents to 4-tert-butylcyclohexanone is preferred,whereas the stereochemical result is inverse when the meta
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.
