A clean break: An N-heterocyclic carbene catalyzes the ring-opening of chiral non-racemic formylcyclopropanes, with simultaneous oxidation of the aldehyde function and without the need for stoichiometric reagents. The activated carboxylate intermediate is trapped by a variety of nucleophiles, thus leading to chiral esters, thioesters, or carboxylic acids (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, EWG=electron- withdrawing group, Nu=nucleophile.)
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Sohn et al. (2006) studied this question.
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