Abstract
Precursors 5-7 of chiral para-methoxybenzyl cations (2-4), which carry a polar substituent (NO2, CN, OH) at the stereogenic α-carbon atom, reacted under acidic conditions with high facial diastereoselectivity (dr = 75:25 to >95:5) to the corresponding 1,1-diarylalkanes threo-9 (50-87% yield). Catalytic amounts of Sc(OTf)3 as Lewis acid were sufficient to convert epoxide 7 into the corresponding alcohols threo-9ca and threo-9cb.
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