753454-02-3Relevant academic research and scientific papers
Double and triple asymmetric induction in phosphaaldol reactions
Kolodiazhna, Anastasia O.,Kukhar, Valery P.,Chernega, Alexander N.,Kolodiazhnyi, Oleg I.
, p. 1961 - 1963 (2004)
A multiple asymmetric induction synthesis was applied to increase the stereoselectivity of the phosphaaldol reaction. The double stereoselectivity was achieved in the reaction of chiral di(1R,2S,5R)-menthyl phosphite 3 with chiral 2,3-D-isopropyliden-(R)-glyceraldehyde 2. The reaction of aldehyde 2 with phosphite 1 in the presence of chiral (R)-ALB catalyst proceeding under stereochemical control of three chiral auxiliaries was the most stereoselective to support the conception of multiplicativity of facial selectivities of chiral reactants involved into the reaction. The stereochemistry of the phosphaaldol reaction was in agreement with Cram's rule. The absolute configuration of the new chiral compounds was established on the basis of NMR and X-ray analysis.
Organic catalysis of phospha-aldol condensation
Kolodyazhnaya,Kukhar,Kolodyazhnyi
experimental part, p. 2043 - 2051 (2009/04/13)
Phospha-aldol reaction of dialkylphosphites with carbonyl compounds is catalyzed by cinchonine alkaloids and thier modified derivatives to give optically active hydroxyphosphonates. The use of diastereomeric pairs of alkaloids allowed obtaining both optic
