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33646586118
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note
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2a but not for 1a. The likely explanation for the lower reactivity of the former (without Cu) is that alkyl substitution considerably increases the strength of the cyclopropane C=C bond. See ref 5a.
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31
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0345711474
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For examples of alkoxide-promoted enantioselective reactions of dialkylzinc and organolithium reagents, see: (b) Vogl, E. M.; Gröger, G.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570.
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33646590665
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note
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The adduct from 3-hydroxymethyl-3-phenylcydopropene gave the lactol in 98% ee after DMF quench (Table 1). Also observed was < 10% of 2 in 50% ee. The low ee for 2 is consistent with enantiomeric enrichment via kinetic resolution.
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36
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0346364994
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