Published January 10, 2018
| Accepted Version + Supplemental Material
Journal Article
Open
Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling
Abstract
An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.
Additional Information
© 2017 American Chemical Society. Received: November 3, 2017. Published: December 4, 2017. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Dr. Michael K. Takase and Mr. Lawrence M. Henling for assistance with X-ray crystallography, as well as Dr. Mona Shahgholi and Naseem Torian for assistance with mass spectrometry measurements. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowship, J.L.H., A.H.C., Grant No. DGE-1144469) and Caltech SURF program (Richard H. Cox and John Stauffer Fellowships, C.M.O.). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01; GM111805-01) is gratefully acknowledged. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms948133.pdf
Supplemental Material - ja7b11707_si_001.pdf
Supplemental Material - ja7b11707_si_002.cif
Supplemental Material - ja7b11707_si_003.cif
Supplemental Material - ja7b11707_si_004.cif
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Additional details
- PMCID
- PMC5851001
- Eprint ID
- 83692
- DOI
- 10.1021/jacs.7b11707
- Resolver ID
- CaltechAUTHORS:20171205-112031343
- DGE-1144469
- NSF Graduate Research Fellowship
- Caltech Summer Undergraduate Research Fellowship (SURF)
- American Cancer Society
- Heritage Medical Research Institute
- R35GM118191-01
- NIH
- GM111805-01
- NIH
- Created
-
2017-12-08Created from EPrint's datestamp field
- Updated
-
2022-03-18Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute