Skip to Main content Skip to Navigation
Journal articles

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

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.
Document type :
Journal articles
Complete list of metadatas

https://hal-normandie-univ.archives-ouvertes.fr/hal-02024492
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:09:30 AM
Last modification on : Thursday, July 2, 2020 - 3:28:58 AM

Identifiers

Citation

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, American Chemical Society, 2018, 20 (9), pp.2757-2761. ⟨10.1021/acs.orglett.8b00984⟩. ⟨hal-02024492⟩

Share

Metrics

Record views

45