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Synthesis and reactivity of bicyclo[3.2.1]octanoid-derived cyclopropanes.

Authors
  • Goodell, John R
  • Poole, Jennifer L
  • Beeler, Aaron B
  • Aubé, Jeffrey
  • Porco, John A Jr
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Dec 02, 2011
Volume
76
Issue
23
Pages
9792–9800
Identifiers
DOI: 10.1021/jo2018922
PMID: 22007996
Source
Medline
License
Unknown

Abstract

Photochemical oxa-di-π-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-π-methane rearrangement of a β,γ-unsaturated iminium. Donor-acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.

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