74181-34-3Relevant articles and documents
Further insights into the organocatalytic reaction of 2,2-dimethyl-1,3-dioxan-5-one with α-silyloxy aldehydes
Sánchez, Dani,Carneros, Héctor,Castro-Alvarez, Alejandro,Llàcer, Enric,Planas, Ferran,Vilarrasa, Jaume
, p. 5254 - 5258 (2016/11/11)
Proline-catalysed reactions of dihydroxyacetone isopropylidene acetal, 1, with enantiopure α-silyloxy aldehydes 2/4/6/8 afford 90–95% yields of cross-aldol products (only one stereoisomer in each case), provided that 15 ± 10 equiv of H2O are pr
Relative tendency of carbonyl compounds to form enamines
Sanchez, Dani,Bastida, David,Bures, Jordi,Isart, Carles,Pineda, Oriol,Vilarrasa, Jaume
supporting information; experimental part, p. 536 - 539 (2012/03/26)
Equilibria between carbonyl compounds and their enamines (from O-TBDPS-derived prolinol) have been examined by NMR spectroscopy in DMSO-d 6. By comparing the exchange reactions between pairs (enamine A + carbonyl B → carbonyl A + enamine B), a quite general scale of the tendency of carbonyl groups to form enamines has been established. Aldehydes quickly give enamines that are relatively more stable than those of ketones, but there are exceptions to this expected rule; for example, 1,3-dihydroxyacetone acetals or 3,5-dioxacyclohexanones (2-phenyl-1,3-dioxan-5-one and 2,2-dimethyl-1,3- dioxan-5-one) show a greater tendency to afford enamines than many α-substituted aldehydes.