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Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles

Cong, Huan and Fu, Gregory C. (2014) Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles. Journal of the American Chemical Society, 136 (10). pp. 3788-3791. ISSN 0002-7863. PMCID PMC3985453. https://resolver.caltech.edu/CaltechAUTHORS:20140304-084532734

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja500706vDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja500706vPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985453/PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2014 American Chemical Society. ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. Received: January 22, 2014. Publication Date (Web): February 27, 2014. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences: R01-GM62871). We thank Yufan Liang, Dr. Allen G. Oliver (University of Notre Dame), Dr. Nathan D. Schley, and Dr. Scott C. Virgil (Caltech Center for Catalysis and Chemical Synthesis, supported by the Gordon and Betty Moore Foundation) for assistance.
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Gordon and Betty Moore FoundationUNSPECIFIED
Issue or Number:10
PubMed Central ID:PMC3985453
Record Number:CaltechAUTHORS:20140304-084532734
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140304-084532734
Official Citation:Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles Huan Cong and Gregory C. Fu Journal of the American Chemical Society 2014 136 (10), 3788-3791
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:44118
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Mar 2014 18:06
Last Modified:03 Oct 2019 06:14

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