Published April 21, 2017
| Accepted Version + Supplemental Material
Journal Article
Open
Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides
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.
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.Attached Files
Accepted Version - nihms948256.pdf
Supplemental Material - ol7b00793_si_001.pdf
Supplemental Material - ol7b00793_si_002.cif
Files
nihms948256.pdf
Additional details
- PMCID
- PMC5868419
- Eprint ID
- 75732
- Resolver ID
- CaltechAUTHORS:20170405-103159884
- DGE-1144469
- NSF Graduate Research Fellowship
- Shionogi & Co., Ltd.
- RGM097582-01
- NIH
- R35GM118191
- NIH
- Created
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2017-04-05Created from EPrint's datestamp field
- Updated
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2022-03-28Created from EPrint's last_modified field