Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphthalene-ytterbium complex

✍ Scribed by Atsushi Nishida; Masamichi Yamanaka; Masako Nakagawa

• Book ID: 104260646
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 252 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02709-9

✦ Synopsis

A new axially chiral ligand, l,l'-(2,2'-bisacylamino)binaphthalene, was found to be effective in the ytterbium-catalyzed asymmetric Diels-Alder reaction between cyclopentadiene and crotonyl-l,3-oxazolidin-2-one. The Diels-Alder reaction using 15 mol% of I,l'-(2,2'-bisbenzoylamino)binaphthaleneoyb(OTf)3o2i-Pr2NEt afforded the adduct with high enantioselectivity (97% yield, endo/exo=91/9, >98% ee for the endo adduct).