A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols

Бредихина, З. А.; Kurenkov, A. V.; Antonovich, Olga A.; Pashagin, Alexander V.; Бредихин, А. А.

doi:10.1016/j.tetasy.2014.05.008

Cited by 8 publications

(1 citation statement)

References 25 publications

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“…17 Although the confirmed structure of 13a was the opposite to that expected for the asymmetric dihydroxylation reaction, it has been occasionally reported depending on the substrate used. 18,19 In this specific substrate, steric hindrance due to the epoxy alcohol interferes with the ordinary interactions with the chiral ligand to direct attack of potassium osmate to the terminal olefin from the less sterically hindered face ( Fig. S-1c).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor

Yoshizawa

Hattori

Kobayashi

et al. 2020

Bioorganic & Medicinal Chemistry

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A B S T R A C TAn octahydroisochromene scaffold has been introduced into a known SARS 3CL protease inhibitor as a novel hydrophobic core to interact with the S2 pocket of the protease. An alkyl or aryl substituent was also introduced at the 1-position of the octahydroisochromene scaffold and expected to introduce additional interactions with the protease. Sharpless-Katsuki asymmetric epoxidation and Sharpless asymmetric dihydroxylation were employed to construct the octahydroisochromene scaffold. The introductions of the P1 site His-al and the substituent at 1-position was achieved using successive reductive amination reactions. Our initial evaluations of the diastereo-isomeric mixtures (16a-d) revealed that the octahydroisochromene moiety functions as a core hydrophobic scaffold for the S2 pocket of the protease and the substituent at the 1-position may form additional interactions with the protease. The inhibitory activities of the diastereoisomerically-pure inhibitors (3a-d) strongly suggest that a specific stereo-isomer of the octahydroisochromene scaffold, (1S, 3S) 3b, directs the P1 site imidazole, the warhead aldehyde, and substituent at the 1-position of the fused ring to their appropriate pockets in the protease.

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Section: Introductionmentioning

confidence: 99%

Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor

Yoshizawa

Hattori

Kobayashi

et al. 2020

Bioorganic & Medicinal Chemistry

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Oxidation and Reduction

Banerji¹

2017

Organic Reaction Mechanisms · 2014

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ChemInform Abstract: A Rare Case of Facial Selectivity Inversion for Sharpless Asymmetric Dihydroxylation in a Series of Structurally Homogeneous Substrates: Synthesis of Non‐racemic 3‐(Nitrophenoxy)‐propane‐1,2‐diols.

et al. 2015

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Substrates: Synthesis of Non--racemic 3-(Nitrophenoxy)-propane-1,2-diols. -Regardless of the reagent used (AD-mix- or AD-mix-), the configuration of the predominant enantiomer formed in the Sharpless asymmetric dihydroxylation of p-and m-nitrophenyl allyl ethers is opposite to the configuration of the product derived from o-nitrophenyl allyl ether. -(BREDIKHINA, Z. A.; KURENKOV, A. V.; ANTONOVICH, O. A.; PASHAGIN, A. V.; BREDIKHIN*, A. A.; Tetrahedron: Asymmetry 25 (2014) 13-14, 1015-1021, http://dx.doi.org/10.

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A rare case of facial selectivity inversion for Sharpless asymmetric dihydroxylation in a series of structurally homogeneous substrates: synthesis of non-racemic 3-(nitrophenoxy)-propane-1,2-diols

Cited by 8 publications

References 25 publications

Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor

Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor

Oxidation and Reduction

ChemInform Abstract: A Rare Case of Facial Selectivity Inversion for Sharpless Asymmetric Dihydroxylation in a Series of Structurally Homogeneous Substrates: Synthesis of Non‐racemic 3‐(Nitrophenoxy)‐propane‐1,2‐diols.

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