202476-53-7

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 164358-21-8 diethyl (1S,2S)-1,2-dihydroxy-2-(4-methoxyphenyl)ethylphosphonate 
• 87750-67-2 (E)-diethyl (4-methoxylstyryl)phosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 1660-94-2 Tetraethyl methylenediphosphonate 

Relevant academic research and scientific papers

Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of vinylphosphonates. An application to the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

The asymmetric dihydroxylation (AD) reaction of vinylphosphonates with AD-mix-α and -β reagents was successfully applied to the enantioselective synthesis of threo-α,β-dihydroxyphosphonates. β-Aryl substituents on the vinyl phosphonates were found to be good directors for the reaction with respect to the yield and enantioselectivity. The utility of chiral α,β-dihydroxyphosphonate 2c was illustrated by the stereocontrolled synthesis of (4S,5S)-4-diethylphosphono-2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane 6, a potentially useful chiron for asymmetric synthesis of α-heteroatom-substituted phosphonates.

Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents

Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD- mix-α or -β reagent was examined to give a series of optically active threo-α,β-dihydroxyphosphonates. Good enantioselectivity (>88% ee) was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carded out with dimethyl phosphonate instead of diethyl phosphonate.