185378-12-5Relevant academic research and scientific papers
Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications
Silva, Franck,Sawicki, Marcin,Gouverneur, Veronique
, p. 5417 - 5419 (2007/10/03)
For the first time, unmodified ynones were used in organocatalytic asymmetric aldol reactions delivering mono-protected anti-α,β- dihydroxyynones in high yields, dr's up to 19:1, and ee's up to 95%. These products can be either reduced to afford enantioen
Hydroxynitrile lyase catalyzed enantioselective HCN addition to O-protected α-hydroxyaldehydes
Roos, Juergen,Effenberger, Franz
, p. 2817 - 2828 (2007/10/03)
Various O-protected glycol- and racemic lactaldehydes 3 and 6 as well as O-allyl protected racemic α-hydroxyaldehydes 7 (R1=Et, Pr, Bu) have been prepared to investigate and perform a stereoselective Kiliani-Fischer synthesis by hydroxynitrile lyase (HNL) catalyzed addition of HCN. From all protecting groups investigated the allyl moiety was most suitable. (R)-PaHNL from bitter almonds (Prunus amygdalus), yielding the (2S)-cyanohydrins 8-10, was found to be a more stereoselective catalyst than (S)-MeHNL from maniok (Manihot esculenta). While (R)-PaHNL led to enantiomeric excesses ≥93%, with (S)-MeHNL the (2R)-cyanohydrins 8-10 were obtained with enantiomeric excesses ≤78%.
