Environmentally friendly selectivity control of enyne metathesis utilizing hydrogen-bonding interaction

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We found that an allylic hydroxy group can activate the adjacent olefin in Ru-alkylidene catalyzed enyne metathesis. The substituent effect could be switched ON/OFF by protection or non-protection of the hydroxy group. By using the switching of the substituent effect, direction control of tandem enyne metathesis of dienynes has been accomplished. The generality of the direction-controlled tandem enyne metathesis was proven by applying to various enyne compounds. Since mechanistic studies suggested that the activation effect of an allylic hydroxy group arises from hydrogen-bonding interaction between the substrate and catalyst, direction control of the tandem enyne metathesis by regulating the hydrogen-bonding interaction was investigated. In this stage, the distinct direction control has not been accomplished completely, but the possibility was shown.