168038-85-5Relevant academic research and scientific papers
Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-statine
Gennari, Cesare,Moresca, Daniela,Vulpetti, Anna,Pain, Gilles
, p. 5593 - 5608 (2007/10/03)
Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacetate-derived chiral enolates and enantiopure N,N-dibenzyl α-amino aldehydes, either the 3,4- anti or the 3,4-syn aldol adduct can be obtained with very high diastereoselectivity just by changing the chiral boron ligand configuration. The above procedure was used for a stereoselective total synthesis of (3S,4S)-statine.
