Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions.
Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in moderate to excellent yields.
Crone
Benedikt
B
Department Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Kirsch
Stefan F
SF
D000478:Alkylation; D003500:Cyclization; D004583:Electrons; D007455:Iodine / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure
D007783:Lactones; D007455:Iodine