ol034731q_si_001.pdf (1.25 MB)
Doyle−Kirmse Reaction of Allylic Sulfides with Diazoalkane-Free (2-Furyl)carbenoid Transfer
journal contribution
posted on 2003-06-24, 00:00 authored by Yumiko Kato, Koji Miki, Fumiaki Nishino, Kouichi Ohe, Sakae UemuraIn the presence of rhodium catalyst, (2-furyl)carbenoids generated from conjugated ene-yne-carbonyl compounds 1 efficiently undergo carbene
transfer reactions with allylic sulfides followed by [2,3]sigmatropic rearrangement of sulfur ylides to give furan-containing sulfides in good
yields. When diallyl sulfide is employed, heteroatom-containing polycyclic compounds are obtained by sequential intramolecular Diels−Alder
cyclization reaction with a constructed furan ring as an enophile.