Concepedia

Gold-Catalyzed Efficient Preparation of Linear α-Iodoenones from Propargylic Acetates

Organic Letters · 2007 · 177 citations · 7 references

Concepts

Inorganic ChemistryAccessible Propargylic AcetatesBroad Substrate ScopeEngineeringAlkene MetathesisPropargylic AcetatesAliphatic Propargylic AcetatesCatalytic SynthesisOrganic ChemistryOrganometallic CatalysisCatalysisChemistryAsymmetric CatalysisBiomolecular Engineering

Abstract

Only 2 mol % of Au(PPh3)NTf2 is needed to convert readily accessible propargylic acetates into versatile linear alpha-iodoenones in good to excellent yields. This reaction is easy to execute and has broad substrate scope. Good to excellent Z-selectivities are observed in the cases of aliphatic propargylic acetates derived from aldehydes.

References

7

Regio‐ and Enantioselective Epoxidation of Dienes by a Chiral Dioxirane: Synthesis of Optically Active Vinyl <i>cis</i>‐Epoxides

Christopher P. Burke, Yian Shi · Angewandte Chemie International Edition · 2006 · 72 citations

Vinyl Cis-epoxides, Chemical Engineering, Enantioselective Synthesis +11

New synthetic applications of organotin compounds: synthesis of stereodefined 2-iodo-2-alkenones, 2-substituted (E)-2-alkenones and 2-methyl-2-cycloalkenones

Fabio Bellina, Adriano Carpita, Donatella Ciucci et al. · Tetrahedron · 1993 · 42 citations

Stereodefined 2-Iodo-2-alkenones, Alkene Metathesis, Organic Chemistry +5

α-Haloenones from secondary alkynols

Geetha J. Angara, Edward McNelis · Tetrahedron Letters · 1991 · 38 citations · Full text

Halogenation, Chemical Engineering, Engineering +7

Synthesis of α-iodo-α,β-unsaturated ketones by the reaction of α-silyl-α,β-unsaturated ketones with ICl or IClAlCl3

Asaf Alimardanov, Ei‐ichi Negishi · Tetrahedron Letters · 1999 · 37 citations

Ring expansions of alkynyl cyclopentanols with iodine and Koser's reagent.

Pakorn Bovonsombat, Edward McNelis · Tetrahedron · 1993 · 36 citations