The stereoselective synthesis of succinamide derivatives via enolate oxidative coupling

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

“…Products analogous to these of the radical homo-coupling above can be obtained by auxiliary controlled oxidative enolate coupling in high yield with good stereocontrol [38–40]. With the auxiliary controlled alkylation of enolates products being analogous to radical hetero-coupling can be synthesized [41–42].…”

Stereoselective coupling of ketone and carboxylate enolates

“…Thus, generation of the lithium enolate of the optically pure butyryloxazolidine 5 (LDA, 278 °C, THF) followed by oxidation (Scheme 5) gave all three possible diastereomers of the dimers upon oxidation with iodine or CuCl 2 . 16 The stereochemical outcome was explained by the intermediacy of a reactive radical pair that collapses in a stereoselective fashion. An S N 2 reaction pathway was ruled out on the basis of the failure of the lithium enolate to react with the preformed optically pure a-iodo derivatives of the starting material 5.…”

Stereoselective Oxidative Dimerization of (1R)-Camphor. A Short Synthesis of exo,exo‘-3,3‘-Biisoborneol

“…Recently, efforts have focused on improving the diastereoselectivity of the carbon−carbon bond forming step. , Reports that acyclic enolates bearing chiral auxiliaries dimerize with high stereoselectivity imply that chiral cyclic enolates would behave the same way. However, the oxidation of norbornanone and camphor enolates was stated 2 to give the exo,exo‘, endo,endo‘, and exo,endo‘ 3,3‘-dimers 4 , 5 , and 6 as a mixture.…”