TY - JOUR T1 - A highly efficient solvent-free asymmetric direct aldol reaction organocatalyzed by recoverable (S)-binam-L-prolinamides. ESI-MS evidence of the enamine-iminium formation. AU - Guillena,Gabriela, AU - Hita,Maria del Carmen, AU - Nájera,Carmen, AU - Viózquez,Santiago F, Y1 - 2008/07/04/ PY - 2008/7/5/pubmed PY - 2008/7/5/medline PY - 2008/7/5/entrez SP - 5933 EP - 43 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 15 N2 - Recoverable (S(a))-binam-L-prolinamide in combination with benzoic acid is used as catalysts in the direct aldol reaction between cycloalkyl, alkyl, and alpha-functionalized ketones and aldehydes under solvent-free reaction conditions. Three different methods are assayed: simple conventional magnetic stirring, magnetic stirring after previous dissolution in THF and evaporation, and ball mill technique. These procedures allow one to reduce not only the amount of required ketone to 2 equiv but also the reaction time to give the aldol products with regio-, diastereo-, and enantioselectivities comparable to those in organic or aqueous solvents. Generally anti-isomers are mainly obtained with enantioselectivities up to 97%. The reaction can be carried out under these conditions also using aldehydes as nucleophiles, yielding after in situ reduction of the aldol products the corresponding chiral 1,3-diols with moderate to high enantioselectivities mainly as anti-isomers. The aldol reaction has been studied by the use of positive ESI-MS technique, providing the evidence of the formation of the corresponding enamine-iminium intermediates. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/18598088/A_highly_efficient_solvent_free_asymmetric_direct_aldol_reaction_organocatalyzed_by_recoverable__S__binam_L_prolinamides__ESI_MS_evidence_of_the_enamine_iminium_formation_ L2 - https://doi.org/10.1021/jo800773q DB - PRIME DP - Unbound Medicine ER -