American Chemical Society
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Competing Domino Processes: Path-Discriminating Ability of Epoxide Stereochemistry at the Angular Position

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posted on 2009-08-20, 00:00 authored by Maurizio Aquino, Imad Safir, Zobida Elkhayat, Zoila Gandara, Manuel Perez, Pascal Retailleau, Siméon Arseniyadis
Structurally different products can be reached selectively from unsaturated vicinal bicyclic diols, which differ only by the epoxide configuration at the angular position. It is possible to modify the regiochemical outcome of the domino process in such a way as to create a different pathway, [4 + 2] versus [4 + 3 + 2], and control product distribution by using the configuration bias. No previous example of a domino variant of the [4 + 3 + 2] process appears to have been documented.