A new chiral oxathiane: synthesis,resolution and absolute configuration determination by vibrational circular dichroism |
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| Institution: | 1. Laboratoire de Stéréochimie Organométallique associé au CNRS, ECPM, Université de Strasbourg, 25 rue Becquerel, 67087 Strasbourg, France;2. Department of Organic Chemistry, Comenius University, Bratislava, Slovakia;3. Chiral Technologies Europe, 67404 Illkirch, France;4. Department of Chemistry, Syracuse University, Syracuse, NY 13244-4100, USA;1. School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051, China;2. Residues and Resource Reclamation Centre, Nanyang Environment and Water Research Institute, Nanyang Technological University, 1 Cleantech Loop, Singapore 637141, Singapore;1. Consiglio Nazionale delle Ricerche – Istituto per la Microelettronica e Microsistemi (CNR-IMM), via Monteroni c/o Campus Universitario, I-73100 Lecce, Italy;2. SENSOR Lab, Department of Information Engineering, Brescia University and CNR-INO, via Valotti, 9, 25133 Brescia, Italy;3. Institute for Energy Research (IREC), Jardí de les Dones de Negre, 1, E-08930 Sant Adrià del Besos, Barcelona, Spain;4. Departament d’Electrònica, Universitat de Barcelona, C.\\ Martí i Franquès 1, E-08028 Barcelona, Spain;1. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People’s Republic of China;2. College of Pharmacy, Guilin Medical University, Guilin, 541004, People’s Republic of China;1. School of Life Science, Beijing Institute of Technology, Beijing, 100081, China;2. School of Computer Science and Engineering, Northeastern University, Shenyang, 110819, China;3. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Science, Chinese Academy of Science, Beijing 100085, China |
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| Abstract: | A new oxathiane, derived from 5-hydroxy-1-tetralone has been synthesized in eight steps, fully characterized as cis-fused rings by 1D and 2D NMR and resolved by preparative chiral chromatography (CHIRALCEL OD-R). The second eluting (+, MeOH)-isomer was assigned (S,S)-configuration by VCD-ab initio simulation. |
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