High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations |
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Authors: | Mühlthau Friedrich Schuster Oliver Bach Thorsten |
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Affiliation: | Lehrstuhl für Organische Chemie I, Technische Universit?t München, Lichtenbergstrasse 4, 85747 Garching, Germany. |
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Abstract: | Chiral carbenium ions can be attacked by arene nucleophiles with high facial diastereoselectivity (dr >/= 94/6). Benzylic cations, such as 2, were generated under acidic conditions and reacted with arenes in intra- and intermolecular Friedel-Crafts alkylation reaction. The depicted reaction 1 --> 3 represents one example for the unprecedented, highly diastereoselective intermolecular Friedel-Crafts alkylation reactions which were observed in this study. |
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