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Published January 27, 2016 | Supplemental Material + Accepted Version
Journal Article Open

Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF_3 Complex


Derivatives of the fully twisted bicyclic amide 7-hypoquinuclidone are synthesized using a Schmidt–Aubé reaction. Their structures were unambiguously confirmed by X-ray diffraction analysis and extensive spectroscopic characterization. Furthermore, the stability and chemical reactivity of these anti-Bredt amides are investigated. 7-Hypoquinuclidonium tetrafluoroborate is shown to decompose to a unique nitrogen bound amide–BF_3 complex of 7-hypoquinuclidone under anhydrous conditions and to react instantaneously with water making it one of the most reactive amides known to date.

Additional Information

© 2015 American Chemical Society. Received: November 9, 2015. Publication Date (Web): December 29, 2015. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. M.L. thanks the Swiss National Science Foundation (SNSF) for a postdoctoral fellowship (P2EZP2_148751). Jonathan Rittle is acknowledged for assistance with the ATR-IR and the Peters group for using their equipment. We are indebted to Dr. Kousouke Tani and Dr. Michael Krout for taking the first steps in creating the twisted amide project and for establishing their synthesis, isolation and crystallization. The authors declare no competing financial interest.

Attached Files

Accepted Version - nihms786605.pdf

Supplemental Material - ja5b11750_si_001.cif

Supplemental Material - ja5b11750_si_002.cif

Supplemental Material - ja5b11750_si_003.cif

Supplemental Material - ja5b11750_si_004.pdf


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