159974-68-2

Upstream product

• 119897-89-1 (R)-3-phenyl-Δ²-isoxazoline-5-methanol 
• 1569-94-4 (3-phenyl-4,5-dihydro-isoxazol-5-yl)-methanol 
• 160024-47-5 (R)-5-Methoxymethyl-3-phenyl-4,5-dihydro-isoxazole 
• 932-90-1 Benzaldoxime 
• 1005327-17-2 (R)-1-phenyl-2-(2-phenyl-1,3,2-dioxaborolan-4-yl)ethanone 
• 156386-82-2 trans-γ-3-benzoylprop-2-en-1-ol 

Downstream Products

• 1005327-16-1 C₁₇H₁₆O₄ 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 109010-59-5 (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 
• 159974-70-6 (2R,4R)-4-phenyl-1,2,4-butanetriol 

Relevant academic research and scientific papers

Chloramphenicol base chemistry. Part 10: Asymmetric synthesis of α-hydroxy chiral alcohols via intramolecular Michael additions of γ-hydroxy-α, β-unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts

We have developed the chloramphenicol base urea-catalyzed intramolecular Michael addition of γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE inhibitor benazepril hydrochloride.

Enantioselective, organocatalytic oxy-Michael addition to γ/δ-hydroxy-α,β-enones: Boronate-amine complexes as chiral hydroxide synthons

An organocatalytic, enantioselective oxy-Michael addition to achiral γ- and δ-hydroxy-α,β-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral β-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction. Copyright

Synthesis of a bifunctional 2,4-dihydroxy five-carbon synthon. Enantiomerically pure Δ2-isoxazolines by chromatographic resolution

Chromatography on cellulose triacetate allows the separation of (R)- and (S)-4,5-dihydro-3-phenyl-5-isoxazolemethanol in 100% ee. Reductive ring cleavage, diastereoselective reduction of the 3-hydroxy ketones thus obtained, and oxidation of the phenyl rin