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The lithium enolates (1) of (R,R)-tartrate acetonides to not decompose with β-elimination; the are stable enough to be alkylated by reactive electrophiles to pentasubstituted trans- and cis-dioxolanes (2) and (3) (80:20), respectively. This reaction provides a route to the synthesis of natural products such as piscidic acid.
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Naef et al. (1981) studied this question.
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