Tandem dienone photorearrangement-cycloaddition for the rapid generation of molecular complexity.

J Am Chem Soc

Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.

Published: November 2013

A tandem dienone photorearrangement-cycloaddition (DPC) reaction of novel cyclohexadienone substrates tethered with various 2π and 4π reaction partners resulted in the formation of polycyclic, bridged frameworks. In particular, use of alkynyl ether-tethered substrates led to (3 + 2) cycloaddition to afford strained alkenes which could be further elaborated by intra- and intermolecular cycloaddition chemistry to produce complex, polycyclic chemotypes.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3964885PMC
http://dx.doi.org/10.1021/ja409992mDOI Listing

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