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    Stereoselective crystallization of 3-(2,6-dimethylphenoxy)propane-1,2-diol: preparation of the single-enantiomer drug mexiletine
    Tetrahedron Asymmetry (2015)
    Zemfira A. BredikhinaAlexey V. KurenkovDmitry B. KrivolapovAlexander A. Bredikhin
    16
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    39
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    10
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    Keywords:
    Enantiopure drug
    Stereocenter
    Recrystallization (geology)
    Mexiletine
    Mitsunobu reaction
    Enantiomeric excess
    Sharpless epoxidation
    Topics:
    Analytical Chemistry and Chromatography
    Asymmetric Synthesis and Catalysis
    Asymmetric Hydrogenation and Catalysis
    Synthesis of Enantiopure 5-Substituted 2,3-Methanopyrrolidines by Cyclization of Enantiopure α-Branched α-N-Homoallylamino Nitriles
    Synlett (2012)
    Fabrice ChemlaFranck FerreiraAlejandro Pérez‐LunaSabrina Ouizem
    The preparation of 5-substituted 2,3-methanopyrrolidines by the stereoselective cyclization of zincated α-amino nitriles derived from enantiopure α-branched homoallylamines has been investigated. The formation of trans adducts in excellent diastereoselectivities (up to >98:2) and good yields (up to 71%) is observed. The absolute configuration and enantiomeric excess are dependent on the nitrogen protecting group.
    Enantiopure drug
    Enantiomeric excess
    Absolute Configuration
    Citations (6)
    Synthesis of enantiopure protected 3-hydroxy-4-amino pyrroline N-oxides
    Tetrahedron Letters (2000)
    Stefano CicchiPaola PonzuoliAndrea GotiAlberto Brandi
    Enantiopure drug
    Pyrroline
    Mitsunobu reaction
    Vicinal
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    ChemInform Abstract: Efficacious and Rapid Metal‐ and Solvent‐Free Synthesis of Enantiopure Oxazolines.
    ChemInform (2015)
    Rym HassaniAlexandre RequetSylvain R. A. MarqueA GaucherDamien Prim
    Abstract The enantiopure oxazolines are synthesized without using any catalysts and solvents from various nitriles and enantiopure amino alcohols under microwave irradiation at high temperature (150 to 240 °C) in short reaction time (60 to 100 min).
    Enantiopure drug
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    Stereoselective synthesis of 5′-hydroxyzearalenone
    Tetrahedron Letters (2018)
    Srilatha AvuluriSheshurao BujaranipalliSaibal DasJ. S. Yadav
    Kinetic resolution
    Ring-Closing Metathesis
    Dihydroxylation
    Mitsunobu reaction
    Sharpless asymmetric dihydroxylation
    Sharpless epoxidation
    Citations (5)
    ChemInform Abstract: Chiral Pyridin‐3‐ones and Pyridines: Syntheses of Enantiopure 2,4‐Disubstituted 6‐Hydroxy‐1,6‐dihydro‐2H‐pyridin‐3‐ones, 2,3‐Disubstituted 4‐Iodopyridines, and Enantiopure 2,3‐Disubstituted 4‐Pyridinemethanols.
    ChemInform (2012)
    Irfan HusainMohammad SaquibVikas BajpaiBrijesh KumarArun K. Shaw
    Abstract A new route to enantiopure dihydropyridines of type (VI) and (XIII) is reported.
    Enantiopure drug
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    First total synthesis of achaetolide
    Tetrahedron Letters (2010)
    S. ChandrasekharSirinyam Venugopal BalajiRajesh Gontla
    Kinetic resolution
    Dihydroxylation
    Mitsunobu reaction
    Ring-Closing Metathesis
    Sharpless epoxidation
    Salt metathesis reaction
    Sharpless asymmetric dihydroxylation
    Triol
    Citations (20)
    Asymmetric total synthesis of 5′-epi-paecilomycin-F
    Tetrahedron Asymmetry (2012)
    Nandan Kumar JanaSamik Nanda
    Mitsunobu reaction
    Ring-Closing Metathesis
    Sharpless asymmetric dihydroxylation
    Sharpless epoxidation
    Dihydroxylation
    Salt metathesis reaction
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    Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: a facile and stereoselective approach
    Tetrahedron Letters (2015)
    Sheshurao BujaranipalliSaibal Das
    Kinetic resolution
    Sharpless epoxidation
    Mitsunobu reaction
    Ring-Closing Metathesis
    Citations (10)
    Synthesis of Enantiopure γ‐Lactones via a RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation of γ‐Keto Acids
    Advanced Synthesis & Catalysis (2018)
    Jing LiYujie MaYufei LuYangang LiuDelong Liu
    Abstract A RuPHOX−Ru catalyzed asymmetric hydrogenation of γ‐keto acids has been developed, affording the corresponding enantiopure γ‐lactones in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 10000 S/C) under the indicated reaction conditions and the resulting products can be transformed to several enantiopure building blocks, biologically active compounds and enantiopure drugs. magnified image
    Enantiopure drug
    Asymmetric hydrogenation
    Reaction conditions
    Citations (24)
    A Valuable Synthetic Route to the Enantiopure Functionalized N‐Substituted Aziridines
    Chinese Journal of Chemistry (2004)
    Sen‐Lan LiJin‐Bo GuoZhao‐Uan YuQinghua Chen
    Abstract Chiral butyrolacto[3,4‐ b ]‐2(S)‐6( R )‐l‐N‐alkylaziridines 7 were synthesized in enantiopure form utilizing racemic 5‐methoxy‐3‐bromo‐2(5 H )furanone (5) and available amines (6) as key precursors. After highly effective reduction of 7, the functionalized 2( S ),3( R )‐dihydroxymethyl‐ N ‐alkylaziridines (8) were obtained in good yields with ≥98% ee . This is a simple and practical method for the preparation of enantiopure aziridines which are important intermediates in the synthesis of biologic active molecules.
    Enantiopure drug
    Citations (1)