High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations.
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.
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.
Friedrich
F
Mühlthau
Oliver
O
Schuster
Thorsten
T
Bach