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Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides

Suzuki, Naoyuki and Hofstra, Julie L. and Poremba, Kelsey E. and Reisman, Sarah E. (2017) Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides. Organic Letters, 19 (8). pp. 2150-2153. ISSN 1523-7060. PMCID PMC5868419. https://resolver.caltech.edu/CaltechAUTHORS:20170405-103159884

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Abstract

An enantioselective Ni-catalyzed cross-coupling of N-hydroxyphthalimide esters with vinyl bromides is reported. The reaction proceeds under mild conditions and uses tetrakis(N,N-dimethylamino)ethylene as a terminal organic reductant. Good functional group tolerance is demonstrated, with over 20 examples of reactions that proceed with >90% ee.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.7b00793DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.7b00793PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5868419PubMed CentralArticle
ORCID:
AuthorORCID
Hofstra, Julie L.0000-0001-9558-4317
Poremba, Kelsey E.0000-0002-7446-257X
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2017 American Chemical Society. Received: March 16, 2017; Published: April 4, 2017. We thank the following Caltech staff for their help: Dr. Scott Virgil of the Caltech Center for Catalysis and Chemical Synthesis for access to experimental and analytical equipment; Dr. Michael K. Takase and Larry M. Henling for assistance in collecting X-ray diffraction data; and Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. We also thank Kevin Sokol and Dr. Alan Cherney (both of Caltech) for preparing NHP esters 6g and 6h and vinyl bromides 1g, 1h, and 1l, respectively. Fellowship support was provided by the National Science Foundation (graduate research fellowship to J.L.H. and K.E.P., Grant No. DGE-1144469) and Shionogi & Co., Ltd. (postdoctoral fellowship to N.S.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (NIGMS RGM097582-01, R35GM118191) is gratefully acknowledged. N.S. and J.L.H. contributed equally to this work. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Shionogi & Co., Ltd.UNSPECIFIED
NIHRGM097582-01
NIHR35GM118191
Issue or Number:8
PubMed Central ID:PMC5868419
Record Number:CaltechAUTHORS:20170405-103159884
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170405-103159884
Official Citation:Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides Naoyuki Suzuki, Julie L. Hofstra, Kelsey E. Poremba, and Sarah E. Reisman Organic Letters 2017 19 (8), 2150-2153 DOI: 10.1021/acs.orglett.7b00793
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75732
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:05 Apr 2017 17:54
Last Modified:03 Oct 2019 16:53

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