Divergent gold-catalysed reactions of cyclopropenylmethyl sulfonamides with tethered heteroaromatics

Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the...

Full description

Saved in:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 55; no. 93; pp. 13971 - 13974
Main Authors Drew, Melanie A, Arndt, Sebastian, Richardson, Christopher, Rudolph, Matthias, Hashmi, A. Stephen K, Hyland, Christopher J. T
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 19.11.2019
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Crystallography
Cycloaddition
Gold
Natural products
Physical Sciences
Science & Technology
Substrates
Sulfonamides
INTRAMOLECULAR CYCLIZATIONS
FUNCTIONALIZATION
ENANTIOSELECTIVE SYNTHESIS
FURAN-YNE
RETRO-BUCHNER REACTION
GOLD(I)-CATALYZED CYCLOISOMERIZATION
CURCUSONES I
RHAMNOFOLANE DITERPENES
VINYL DIAZO DERIVATIVES
3+2 CYCLOADDITION
Online AccessGet full text

Cover

More Information
Summary:Cyclopropenylmethyl sulfonamides with tethered heteroaromatics have been demonstrated to undergo divergent gold-catalysed cyclisation reactions. A formal dearomative (4+3) cycloaddition takes place with furan-tethered substrates, yielding densely functionalised 5,7-fused heterocycles related to the bioactive curcusone natural products. Indole-tethered substrates display divergent reactivity giving biologically important tetrahydro-β-carbolines via a Friedel-Crafts mechanism. Cyclopropenylmethyl sulfonamides with tethered heteroaromatics can undergo divergent gold-catalysed cyclisation reactions based on the nature of the aromatic tether.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/c9cc06241f
1909426
1909427
and
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc06241f