Total Synthesis of (R,R,R)‐α‐Tocopherol Through Asymmetric Cu‐Catalyzed 1,4‐Addition |
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| Authors: | Dr Andreas Ole Termath B Sc Hanna Sebode M Sc Waldemar Schlundt Dr René T Stemmler Dr Thomas Netscher Priv‐Doz Dr Werner Bonrath Prof Dr Hans‐Günther Schmalz |
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| Institution: | 1. Universit?t zu K?ln, Department für Chemie, Greinstrasse 4, 50939 K?ln (Germany);2. DSM Nutritional Products, Research and Development, P.O. Box 2676, 4002 Basel (Switzerland) |
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| Abstract: | By introducing a disposable activating substituent at C‐3, the asymmetric 1,4‐addition to a notoriously unreactive 2‐substituted chromenone was achieved with high levels of (2R)‐stereoselectivity in the presence of a chiral CuI‐phosphoramidite complex as a catalyst. This paved the way for an efficient and conceptually novel synthesis of (R,R,R)‐α‐tocopherol from readily available starting materials. |
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| Keywords: | asymmetric conjugate addition copper catalysis chiral ligands chromenones vitamin E |
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