Tandem Michael Addition/Ylide Epoxidation for the Synthesis of Highly Functionalized Cyclohexadiene Epoxide Derivatives
- 1 April 2008
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (16) , 5408-5409
Abstract
A highly efficient diastereoselective synthesis of cyclohexadiene epoxide derivatives with a multi-stereocenter has been developed via a tandem ylide Michael addition/epoxidation. By employing a chiral sulfonium ylide, up to 96% ee can be achieved in good yields.Keywords
This publication has 43 references indexed in Scilit:
- Chalcogenides as OrganocatalystsChemical Reviews, 2007
- The Use of Vinyl Sulfonium Salts in the Stereocontrolled Asymmetric Synthesis of Epoxide‐ and Aziridine‐Fused Heterocycles: Application to the Synthesis of (−)‐BalanolAngewandte Chemie International Edition, 2006
- Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid OrganocatalystsAngewandte Chemie International Edition, 2006
- Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidinesChemical Communications, 2006
- Telluronium and Sulfonium Ylides for Organic TransformationSynlett, 2005
- Enantioselective Organocatalytic Cyclopropanation via Ammonium YlidesAngewandte Chemie International Edition, 2004
- Catalytic, Asymmetric Sulfur Ylide-Mediated Epoxidation of Carbonyl Compounds: Scope, Selectivity, and Applications in SynthesisAccounts of Chemical Research, 2004
- Stereoselective Cyclopropanation ReactionsChemical Reviews, 2003
- Stereoselective synthesis of three-membered ring compounds via ylide routesPure and Applied Chemistry, 1999
- Asymmetric Ylide Reactions: Epoxidation, Cyclopropanation, Aziridination, Olefination, and RearrangementChemical Reviews, 1997