Org Lett
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, United States.
Published: July 2017
Site- and regiocontrolled Au-catalyzed allene carbocyclizations furnish highly substituted cyclopentenes in >1:1 dr. Significant substitution on the substrate is tolerated, with potential to install five contiguous stereocenters after alkene functionalization. Major challenges include identifying a Au/Cu catalyst that controls both the relative rates of allene epimerization/cyclization and the facial selectivity in addition of a metal enolate to the allene. Experiments to achieve stereodivergent cyclizations and transform key cyclopentenes into useful synthetic building blocks are described.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5542682 | PMC |
http://dx.doi.org/10.1021/acs.orglett.7b01350 | DOI Listing |
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