Stereoselectivity in the organoiron-mediated synthesis of (±)-mesembrine |
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| Authors: | Caroline Roe G Richard Stephenson Christopher E Anson |
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| Institution: | a Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy University of East Anglia, Norwich NR4 7TJ, UK
b Institut für Anorganische Chemie der UniversitätKarlsruhe, Engesserstrasse 15, D-76128 Karlsruhe, Germany |
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| Abstract: | The preparation and structural characterisation of a 1-aryl-substituted electrophilic η5-cyclohexadienyliron complex with the correct functionalisation as a ‘C12 building block’ for the synthesis of (±)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine. |
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| Keywords: | Asymmetric synthesis Organometallic electrophiles Tricarbonyliron Mesembrine |
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