Treatment of the pure enantiomer 1 with methyllithium furnishes via cycloallene 2 its dimer 3 with high selectivity. In contrast, racemic 1 yielded only 5 % of 3 and 95 % of the cis isomer of 3. Thus, racemic 2 is an example of molecular recognition of remarkable selectivity.
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Christl et al. (2000) studied this question.
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