Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition |
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| Institution: | 1. Department of Chemistry, Panjab University, India;2. Department of Microbiology, Panjab University, Chandigarh 160014, India;3. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;1. Department of Chemistry, University of Botswana, Private Bag 0022, Gaborone, Botswana;2. Institute of Environmental Research (INFU), Department of Chemistry and Chemical Biology, Chair of Environmental Chemistry and Analytical Chemistry, TU Dortmund, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany;3. Department of Chemistry, University of Kinshasa, P.O. Box: 190 Kinshasa XI, Congo;1. Department of Chemistry, University of Kalyani, Kalyani, West Bengal 741235, India;2. Department of Chemical Sciences, Indian Institute of Science Education & Research Kolkata, Mohanpur, West Bengal 741246, India;3. Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India;4. Institut fur Anorganische Chemie und Analytische Chemie, Johannes-Gutenberg Universitat Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany;1. Department of Biopharmaceutics, Graduate School of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan;2. Department of Biopharmaceutics, College of Pharmacy, Kinjo Gakuin University, Nagoya, Japan;3. Department of Biopharmaceutics, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Tokyo, Japan;1. MINOS-EMaS, Universitat Rovira i Virgili, Avda. Països Catalans 26, 43007 Tarragona, Spain;2. Central European Institute of Technology (CEITEC), Brno University of Technology, Technická 10, 616 00 Brno, Czech Republic;3. Scientific Service, Universitat Rovira i Virgil, Avda. Països Catalans 26, 43007 Tarragona, Spain;4. Division of Materials Chemistry, Faculty of Engineering, Hokkaido University, N-13, W-8, Sapporo 060-8628, Japan;1. Chemistry Department, University of Pretoria, Private Bag X20, Hatfield 0028, Pretoria, South Africa;2. Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg 2050, South Africa |
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| Abstract: | Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoylcamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compounds can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol and its enantiomer. |
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