Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
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Cong-2014-Catalytic Enantioselective.pdf
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Author(s)
Cong, Huan
Fu, Gregory C.
Date Issued
March 2014
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Cong, Huan, and Gregory C. Fu. “Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles.” Journal of the American Chemical Society 136, no. 10 (March 12, 2014): 3788–3791. © 2014 American Chemical Society.
Version
Final published version
Abstract
As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if β-migratory insertion proceeds faster than direct cross-coupling, an additional carbon–carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are commercially available), we have established the viability of this approach for the catalytic asymmetric synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a β-migratory insertion and one that begins as a mixture of enantiomers.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja500706v
