Pd-Catalyzed Coupling of Propargylic Oxiranes with Arylboronic Acids

Significance

Allenols are widely represented among natural products and also are useful synthetic intermediates. The usual approach to this class of compounds is the reaction of propargylic oxiranes with organometallic reagents. The described method allows the use of stable and often commercially available arylboronic acids instead of organometallic reagents for the synthesis of substituted 2,3-allenols. The starting oxiranes are readily prepared by epoxidation of enynes. For chiral substrates the method of Shi et al. can be used.