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

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

SUBMITTER: Goodell JR

PROVIDER: S-EPMC3235415 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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

Goodell John R JR Poole Jennifer L JL Beeler Aaron B AB Aubé Jeffrey J Porco John A JA

The Journal of organic chemistry 20111101 23

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. ...[more]

PMID: 22007996

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