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Ruthenium-catalyzed cycloisomerizations of diynols
Barry M Trost1, Michael T Rudd
1Department of Chemistry, Stanford University, Stanford, CA 94305, USA. bmtrost@stanford.edu
Abstract:
A wide variety of diynols containing tertiary, secondary, and primary propargylic alcohols undergo a cycloisomerization reaction to form dienones and dienals in the presence of a catalytic amount of [CpRu(CH(3)CN)(3)]PF(6). The formation of five- and six-membered rings is possible using this methodology. Secondary diynols react to form single geometrical isomeric dienones and -als. Primary diynols undergo a cycloisomerization as well as a hydrative cyclization process. The utility of primary diynol cycloisomerization is demonstrated in a synthesis of (+)-alpha-kainic acid.
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