Alkynyliodonium Salts in Organic Synthesis. Preparation of Annelated Dihydropyrroles by Cascade Addition/Bicyclization of Dienyltosylamide Anions with Phenyl(propynyl)iodonium Triflate
The Journal of Organic Chemistry1999Vol. 64(15), pp. 5650–5660
Citations Over TimeTop 10% of 1999 papers
Abstract
The addition of simple pentadienyltosylamide derivatives to the two-carbon electrophile phenyl(propynyl)iodonium triflate initiates a sequence of transformations that furnishes complex, highly functionalized cyclopentenannelated dihydropyrrole products in moderate yields with complete stereoselection. This sequence demonstrates that diyls resulting from homolytic scission of alkylidene carbene-alkene adducts can be readily accessed under mild experimental conditions and that, in the presence of appropriate pendant functionality, these diyls can productively cyclize. The isomeric isoprene-derived tosylamides follow an abbreviated reaction course and deliver azabicyclo[3.1.0]hexanes via an isomerization that competes with diyl formation.
Related Papers
- → Catalytic, contra -Thermodynamic Positional Alkene Isomerization(2021)88 cited
- → Reactivity and Selectivity of 1,3-Diyn-6-enes in Electrophilic Transition Metal-Catalyzed Reactions(2006)55 cited
- → Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives(2018)16 cited
- → ChemInform Abstract: The Friedel‐Crafts Chemistry: Acetates of the Baylis‐Hillman Adducts as Novel Stereodefined β‐Electrophiles.(1996)
- → Catalytic, contra-Thermodynamic Alkene Isomerization(2021)