The selective protonation of one enantiomer in a racemic mixture of allenylmetal compounds is possible with Pd0/SmI2 and a chiral alcohol (see reaction scheme below). The products, enantiomerically pure allenic esters, are an important class of natural products and synthetic intermediates. This type of dynamic kinetic resolution by asymmetric protonation is an effective method for the asymmetric synthesis of allenes from racemic allenyl-/propargylmetal compounds.
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Mikami et al. (1997) studied this question.
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