Cyclopropane Intermediates from Insertion Reactions of Platinum-Carbenes: A Route to Heterospiranes

Kiseong Kim, Soyung Kim, Chang Ho Oh

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Heteroaromatic-anchored enynals with a pendent alkene group were successfully cyclized through a Huisgen-type [3+2] cycloaddition to give a tetracyclic Pt-carbene complex that underwent insertion into the C-H bond in the β-position to give fused cyclopropanes that are otherwise inaccessible. On heating, the cyclopropanes smoothly rearranged to form the corresponding heterospiranes with excellent levels of stereoselectivity and high yields.

Original languageEnglish
Article numberst-2017-u0595-l
Pages (from-to)354-358
Number of pages5
JournalSynlett
Volume29
Issue number3
DOIs
StatePublished - 2018 Feb 13

Fingerprint

Cyclopropanes
Platinum
Stereoselectivity
Cycloaddition
Alkenes
Heating
cyclopropane
carbene

Keywords

  • carbenes
  • cyclization
  • heterospiranes
  • platinum catalysis
  • pyrylium ions

Cite this

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Cyclopropane Intermediates from Insertion Reactions of Platinum-Carbenes : A Route to Heterospiranes. / Kim, Kiseong; Kim, Soyung; Oh, Chang Ho.

In: Synlett, Vol. 29, No. 3, st-2017-u0595-l, 13.02.2018, p. 354-358.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Cyclopropane Intermediates from Insertion Reactions of Platinum-Carbenes

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AU - Kim, Kiseong

AU - Kim, Soyung

AU - Oh, Chang Ho

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AB - Heteroaromatic-anchored enynals with a pendent alkene group were successfully cyclized through a Huisgen-type [3+2] cycloaddition to give a tetracyclic Pt-carbene complex that underwent insertion into the C-H bond in the β-position to give fused cyclopropanes that are otherwise inaccessible. On heating, the cyclopropanes smoothly rearranged to form the corresponding heterospiranes with excellent levels of stereoselectivity and high yields.

KW - carbenes

KW - cyclization

KW - heterospiranes

KW - platinum catalysis

KW - pyrylium ions

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