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

Author(s)
McGeough, Catherine P.; Strom, Alexandra E.; Jamison, Timothy F
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Abstract
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.
Date issued
2019-05
URI
https://hdl.handle.net/1721.1/125989
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
McGeough, Catherine P. et al., "Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes." Organic Letters 21, 10 (May 2019): p. 3606–09 doi. 10.1021/acs.orglett.9b01019 ©2019 Authors
Version: Author's final manuscript
ISSN
1523-7052
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