Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes

Skipped polyenes featuring high (E)-selectivity and varying methyl substitution patterns are synthesized using a nickel-catalyzed cross-coupling reaction between allyl trifluoroacetates and vinyl bromides. The utility of this cross-electrophile coupling is showcased in part by the synthesis of the R...

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Bibliographic Details
Main Authors: McGeough, Catherine P., Strom, Alexandra E., Jamison, Timothy F
Other Authors: Massachusetts Institute of Technology. Department of Chemistry
Format: Article
Language:English
Published: American Chemical Society (ACS) 2020
Online Access:https://hdl.handle.net/1721.1/125989
Description
Summary:Skipped polyenes featuring high (E)-selectivity and varying methyl substitution patterns are synthesized using a nickel-catalyzed cross-coupling reaction between allyl trifluoroacetates and vinyl bromides. The utility of this cross-electrophile coupling is showcased in part by the synthesis of the RST fragment of the marine ladder polyether, maitotoxin. Construction of this fragment is particularly challenging due to the alternating methyl substitution pattern. ©2019 American Chemical Society.