Straightforward Entry toward Highly Substituted 2,3-Dihydrobenz[b]oxepines by Ring Expansion of Benzopyryliums with Donor-Acceptor Diazo Compounds - Archive ouverte HAL Access content directly
Journal Articles Organic Letters Year : 2018

Straightforward Entry toward Highly Substituted 2,3-Dihydrobenz[b]oxepines by Ring Expansion of Benzopyryliums with Donor-Acceptor Diazo Compounds

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1

Abstract

Ylide-type reactivity of diazo compounds is exploited in a new way to prepare benzo[b]oxepines thanks to the formation of three chemical bonds and two contiguous and highly substituted stereocenters in a single pot. This cationic reaction cascade first involves addition of a donor–acceptor-substituted diazo compound to a benzopyrylium. Selective 1,2 migration of the endocyclic C–C bond then results in a ring-expansion and generates a second oxocarbenium that is trapped by a nucleophile added sequentially.
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hal-02024492 , version 1 (19-02-2019)

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Thibaut Courant, Morgane Pasco, Thomas Lecourt. Straightforward Entry toward Highly Substituted 2,3-Dihydrobenz[b]oxepines by Ring Expansion of Benzopyryliums with Donor-Acceptor Diazo Compounds. Organic Letters, 2018, 20 (9), pp.2757-2761. ⟨10.1021/acs.orglett.8b00984⟩. ⟨hal-02024492⟩
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