673491-82-2Relevant academic research and scientific papers
Solvent-free direct enantioselective aldol reaction using polystyrene-supported N-sulfonyl-(Ra)-binam-d-prolinamide as a catalyst
Banon-Caballero, Abraham,Guillena, Gabriela,Najera, Carmen
experimental part, p. 1599 - 1606 (2010/12/25)
The immobilization of N-sulfonyl-(Ra)-binam-d-prolinamide using polystyrene as a support allows the recovery of an efficient catalytic system for the enantioselective direct aldol reaction between different ketones and aldehydes under solvent-f
Unusual reversal of regioselectivity in antibody-mediated aldol additions with unsymmetrical methyl ketones
Maggiotti,Bahmanyar,Reiter,Resmini,Houk,Gouverneur
, p. 619 - 632 (2007/10/03)
A catalytic regio- and enantioselective aldol reaction of various unsymmetrical methyl ketones with para-nitrobenzaldehyde has been developed using aldolase antibodies as the catalysts. It has been found that the sense and level of regioselectivity for the reactions catalysed by antibody 38C2 and 33F12 are highly dependent on the structure of both the donor and the acceptor but in contrast, antibodies 84G3 and 93F3 catalyse the exclusive formation of the linear regioisomer independent of the structure of the reactants examined. The level of enantiocontrol is very high for most reactions. Both linear aldol enantiomers could be accessed through aldol or retro-aldol reactions using the same antibody. Theoretical studies on regioisomeric α- and β-heteroatom substituted enamines derived from unsymmetrical ketones suggest that most of the linear aldol products formed in the presence of antibodies 84G3 and 93F3 must be formed from intermediate enamines which are not the thermodynamically most favourable.
A biocatalytic route to enantioenriched, sulfanyl aldol products
Baker-Glenn,Ancliff,Gouverneur
, p. 7607 - 7619 (2007/10/03)
The aldol products derived from sulfur- or selenium containing acceptors were prepared by kinetic resolution in the presence of antibody 84G3 with enantiomeric excesses ranging from 56 to 70%. Much higher level of enantioselectivity was obtained (enantiomeric excesses all superior to 96%) for sulfanyl aldol products derived from thiomethoxyacetone with three different acceptors.
