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

Thomas R. Hoye; Christopher J. Dinsmore

doi:10.1016/0040-4039(92)88041-3

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

Thomas R. Hoye, Christopher J. Dinsmore

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	169-172
Number of pages	4
Journal	Tetrahedron Letters
Volume	33
Issue number	2
DOIs	https://doi.org/10.1016/0040-4039(92)88041-3
State	Published - 1992

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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.",

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AU - Dinsmore, Christopher J.

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AB - 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.

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

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