Highly enantioselective Diels–Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex

✍ Scribed by Shinji Harada; Nozomi Toudou; Shiharu Hiraoka; Atsushi Nishida

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 389 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.07.110

✦ Synopsis

The synthesis and utility of the novel axially chiral bis-urea ligand BINUREA are described. A complex of this urea ligand with ytterbium triflate and DBU can be used in the catalytic enantioselective Diels-Alder reaction of Danishefsky-type diene and electron-deficient olefins to give the adducts in good to excellent yield and enantiomeric excess (ee).