Organic Letters
Organic Letters
5 years ago

Diastereoselective Au-Catalyzed Allene Cycloisomerizations to Highly Substituted Cyclopentenes

Diastereoselective Au-Catalyzed Allene Cycloisomerizations to Highly Substituted Cyclopentenes
Jennifer M. Schomaker, William A. T. Raimbach, Alicia M. Phelps, Ryan D. Reeves
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01350

DOI: 10.1021/acs.orglett.7b01350

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