Tandem alkyne insertion and allyl sulfonium ylide rearrangement of γ,δ-alkynyl-α′-diazoketones

Thomas R. Hoye, Christopher J. Dinsmore

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

Acetylenic α-diazoketones 1, when treated with catalytic rhodium carboxylate dimer and diallylsulfide (1.1 equiv), undergo sequential alkyne insertion/ylide formation/sigmatropic rearrangement to give γ-allylthio cyclic enones. This transformation was used to probe the influence of alkyne substituents on 5-exo vs. 6-endo cyclization selectivity in the alkyne insertion event.

Original languageEnglish (US)
Pages (from-to)169-172
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number2
DOIs
StatePublished - 1992

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