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Published May 7, 2021 | Accepted Version + Supplemental Material
Journal Article Open

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


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.

Additional Information

© 2021 American Chemical Society. Received: March 4, 2021; Published: 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.

Attached Files

Accepted Version - nihms-1746783.pdf

Supplemental Material - ol1c00763_si_001.pdf


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August 20, 2023
October 23, 2023