Enantioselective Diels-Alder reactions catalyzed by chiral 1,1′-(2,2′-bisacylamino)binaphthalene-ytterbium complex
1999; Elsevier BV; Volume: 40; Issue: 8 Linguagem: Inglês
10.1016/s0040-4039(98)02709-9
ISSN1873-3581
AutoresAtsushi Nishida, Masamichi Yamanaka, Masako Nakagawa,
Tópico(s)Marine Sponges and Natural Products
ResumoA new axially chiral ligand, 1,1′-(2,2′-bisacylamino)binaphthalene, was found to be effective in the ytterbium-catalyzed asymmetric Diels-Alder reaction between cyclopentadiene and crotonyl-1,3-oxazolidin-2-one. The Diels-Alder reaction using 15 mol% of 1,1′-(2,2′-bisbenzoylamino)binaphthalene·Yb(OTf)3·2i-Pr2NEt afforded the adduct with high enantioselectivity (97% yield, endoexo=919, >98% ee for the endo adduct).
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