4.7 Article

Synthesis and Reactivity of Bicyclo[3.2.1]octanoid-Derived Cyclopropanes

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 23, Pages 9792-9800

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2018922

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Funding

  1. NIGMS CMLD Initiative [P50 GM067041, P50 GM69663]

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Photochemical oxa-di-pi-methane rearrangement of bicyclo[3.2.1]octanoid scaffolds affords multifunctional, donor acceptor cyclopropanes. A related photochemical reaction of an iminium ether substrate uncovered an unprecedented aza-di-pi-methane rearrangement of a beta,gamma-unsaturated iminium. Donor acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.

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