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A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement

Han, Seo-Jung and Cavitt, Marchello A. and Stoltz, Brian M. (2021) A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement. Organic Letters . ISSN 1523-7060. doi:10.1021/acs.orglett.1c00763. (In Press) https://resolver.caltech.edu/CaltechAUTHORS:20210416-080746750

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Abstract

Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This operationally simple reaction is tolerant of many functional groups and applicable to the synthesis of various medium-sized ring nitrogen-containing heterocycles.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.1c00763DOIArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2021 American Chemical Society. Received: March 4, 2021; Publication Date: April 12, 2021. We thank the NIH-NIGMS (R01GM080269) and Caltech for financial support. S.-J.H. was supported by the Korea Institute of Science and Technology (2E31360, 2E31140) and the NRF (NRF-2020M1A2A2079798). M.A.C. thanks the California Alliance for Graduate Education and the Professoriate (AGEP) and the NSF (Grant No. 1306760). We thank Dr. Trevor Lohrey for mass spectrometry assistance. Author Contributions: S.-J.H. and M.A.C. contributed equally to this work. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
Korea Institute of Science and Technology (KIST)2E31360
Korea Institute of Science and Technology (KIST)2E31140
National Research Foundation of KoreaNRF-2020M1A2A2079798
California Alliance for Graduate Education and the ProfessoriateUNSPECIFIED
NSFHRD-1306760
DOI:10.1021/acs.orglett.1c00763
Record Number:CaltechAUTHORS:20210416-080746750
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210416-080746750
Official Citation:A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement. Seo-Jung Han, Marchello A. Cavitt, and Brian M. Stoltz. Organic Letters. Article ASAP; DOI: 10.1021/acs.orglett.1c00763
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:108750
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 Apr 2021 16:30
Last Modified:19 Apr 2021 16:30

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