Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases.
Chiral alpha-aminophosphonates have been synthesized and their performance was evaluated as organocatalysts in the direct asymmetric aldol reaction. High enantioselectivities (up to 99% ee) were achieved for a range of substituted cyclohexanones and benzaldehydes. Several organic bases, such as DBU, DBN, and TMG, were used together with the alpha-aminophosphonates in the aldol reactions and were found to favor syn-selectivity.
Dinér
Peter
P
Organic Chemistry, Department of Chemistry, Göteborg University, SE-412 96 Göteborg, Sweden.
Amedjkouh
Mohamed
M
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics
D000588:Amines; D001547:Benzaldehydes; D003512:Cyclohexanones; D063065:Organophosphonates