A practical method for synthesis of terminal 1,2-diols in high enantiomeric excess via oxazaborolidine-catalyzed asymmetric reduction |
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| Affiliation: | 1. Departament de Química, Universitat Autònoma de Barcelona, 08193, Cerdanyola del Vallès, Spain;2. Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, 08193, Cerdanyola del Vallès, Spain;1. Univ. Lille, Inserm, CHU Lille, UMR-S 1172 JPArc Centre de Recherche Jean-Pierre AUBERT Neurosciences et Cancer, F-59000 Lille, France;2. Univ. Lille, Inserm, CHU Lille, U995 LIRIC Lille Inflammation Research International Center, F-59000 Lille, France;1. Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu, 501-1196, Japan;2. Saida FDS, Inc., 143-10 Isshiki, Yaizu, 425-0054, Japan;3. Laboratory of Organic Chemistry, Daiichi University of Pharmacy, 22-1 Tamagawa-cho, Minami-ku, Fukuoka, 815-8511, Japan;1. Research Unit on BioActive Molecules, Department of Biomedicinal Chemistry, Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), Jordi Girona 18-26, E-08034 Barcelona, Spain;2. University of Barcelona (UB), Faculty of Pharmacy, Department of Pharmacology and Medicinal Chemistry, Unit of Pharmaceutical Chemistry (Associated Unit to CSIC), Avga. Joan XXIII s/n, E-08028 Barcelona, Spain |
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| Abstract: | Asymmetric borane reduction of α-hydroxy ketones protected with a tetrahydropyranyl (THP) group catalyzed by Corey's CBS reagent using N-phenylamine–borane complexes as the hydride source provided the corresponding terminal 1,2-diols with a very high enantiomeric excess. |
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