High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations

Friedrich Mühlthau; Oliver Schuster; Thorsten Bach

doi:10.1021/ja050626v

High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations

J Am Chem Soc. 2005 Jul 6;127(26):9348-9. doi: 10.1021/ja050626v.

Authors

Friedrich Mühlthau¹, Oliver Schuster, Thorsten Bach

Affiliation

¹ Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.

PMID: 15984844
DOI: 10.1021/ja050626v

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.