89300-47-0Relevant academic research and scientific papers
STEREOSELECTIVE SYNTHESIS OF SOME CIS 2,3-DISUBSTITUTED CYCLANONES RING SIZE INFLUENCE ON THE STEREOSELECTIVITY OF 2-SUBSTITUTED ENDOCYCLIC ENOLATES PROTONATION
Hatzigrigoriou, E.,Wartski, L.,Seyden-Penne, J.,Toromanoff, E.
, p. 5045 - 5050 (1985)
Conjugate addition of carbanionic reagents formed from aryl- or phenyl-thioacetonitriles 1a-c and 2 to 2-methyl and 2-phenyl 2-cyclohexenone or 2-methyl 2-cyclopentenone, followed by acidic quench, under kinetic control, leads to different ratios of cis and trans 2,3-disubstituted cyclanones according to ring size.From 2-methyl and 2-phenyl 2-cyclohexenone, the cis isomer is highly predominant (85 to 98percent).From 2-methyl 2-cyclopentanone a cis/trans mixture is obtained: the cis isomer only predominates when a bulky reagent (1c) is used (80percent); in the other cases a mixture of nearly 1:1 is obtained.
ADDITION CONJUGUEE-ALKYLATION: STEREOCHIMIE DE LA REACTION DES LITHIENS D'ARYLACETONITRILES SUR LES CYCLENONES SUIVIE DU PIEGEAGE PAR L'IODURE DE METHYLE EN UNE SEULE OPERATION
Hatzigrigoriou, Evagelia,Roux-Schmitt, Marie-Claude,Wartski, Lya,Seyden-Penne, Jacqueline,Merienne, Claude
, p. 3415 - 3418 (2007/10/02)
The stereochemistry of trapping of enolates, resulting from reaction of lithiated arylacetonitriles to cyclenones, by methyl iodide, is examined.In a medium such as THF-HMPT, the trans 2,3-disubstituted cyclanones are obtained with good yields, and moreover in nearly all cases alkylation takes place under kinetic control.
