159974-67-1Relevant 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
Wang, Haifeng,Yan, Linjie,Wu, Yan,Chen, Fener
, p. 2793 - 2800 (2017/04/14)
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.
Hydroxyl group-directed organocatalytic asymmetric michael addition of α,β-unsaturated ketones with alkenylboronic acids
Inokuma, Tsubasa,Takasu, Kiyosei,Sakaeda, Toshiyuki,Takemoto, Yoshiji
supporting information; experimental part, p. 2425 - 2428 (2009/11/30)
The organocatalytic asymmetric Michael addition of organoboronic acids to ?-hydroxy enones in the presence of an iminophenol-type thiourea catalyst is demonstrated. The hydroxyl group in the substrates plays a critical role in this reaction.
Synthesis of a bifunctional 2,4-dihydroxy five-carbon synthon. Enantiomerically pure Δ2-isoxazolines by chromatographic resolution
Ticozzi, Calimero,Zanarotti, Antonio
, p. 7421 - 7424 (2007/10/02)
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
