doi: 10.1021/ja050626v.
High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations
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- PMID: 15984844
- DOI: 10.1021/ja050626v
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High facial diastereoselectivity in intra- and intermolecular reactions of chiral benzylic cations
J Am Chem Soc.
.
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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