427875-98-7Relevant articles and documents
Diastereo- and enantioselective direct catalytic aldol reaction of 2-hydroxyacetophenones with aldehydes promoted by a heteropolymetallic complex: Catalytic asymmetric synthesis of anti-1,2-diols
Yoshikawa, Naoki,Suzuki, Takeyuki,Shibasaki, Masakatsu
, p. 2556 - 2565 (2002)
An anti-selective direct catalytic asymmetric aldol reaction of 2-hydroxyacetophenones with aldehydes is described. The reaction is catalyzed by a heteropolymetallic complex to afford anti-α,β-dihydroxy ketones as the major diastereomer with excellent enantioselectivity. The use of 2-hydroxyacetophenones bearing electron-donating groups at the phenyl moiety enabled efficient transformation of the aldol products (α,β-dihydroxy ketones) into the corresponding α,β-dihydroxy ester derivatives via Baeyer-Villiger oxidation. A plausible reaction mechanism is also discussed based on the stereochemistry of the products.
