Scope and Mechanism of the (4+3) Cycloaddition Reaction of Furfuryl Cations

• Published in: Angewandte Chemie International Edition Vol. 50; no. 50; pp. 11990 - 11993
• Main Authors: Winne, Johan M., Catak, Saron, Waroquier, Michel, Van Speybroeck, Veronique
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.12.2011; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: carbocations; Cationic; Cations; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; DFT calculations; Dienes; furans; Furfuryl alcohol; fused-ring systems; Lewis acid; Mathematical analysis; Physical Sciences; Science & Technology; ALLYL CATIONS; fused-ring systems; FURAN; cycloaddition; STEREOSELECTIVITY; carbocations; furans; INTERMEDIATE; OXYALLYL CATIONS; DFT calculations

It all adds up: Furfuryl alcohols are revealed as direct reaction partners for a wide range of conjugated dienes in a (4+3) cycloaddition motif (see scheme). This novel Lewis acid promoted process gives straightforward access to various polycyclic skeletons containing a seven‐membered ring. A plausi...