1403496-64-9Relevant academic research and scientific papers
Pd-catalyzed threefold arylation of Baylis-Hillman bromides and acetates with triarylbismuth reagents
Rao, Maddali L. N.,Giri, Somnath
, p. 4580 - 4589 (2012/11/07)
Functionalized alkyl 2-benzylacrylates and 2-benzylacrylonitriles were synthesized by means of atom-economic cross-couplings of Baylis-Hillman bromides or acetates with BiAr3 under palladium-catalyzed conditions. These reactions, involving thre
On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering
Brenna, Elisabetta,Fronza, Giovanni,Fuganti, Claudio,Gatti, Francesco G.,Manfredi, Alessia,Parmeggiani, Fabio,Ronchi, Paolo
, p. 94 - 101 (2012/10/30)
The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes, as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction.
