Rapid Assembly of Tetrasubstituted Furans via Pummerer-Type Rearrangement
Franz‐Lucas Haut, Christoph Habiger, Lukas A. Wein, Klaus Wurst, Maren Podewitz, Thomas Magauer
Abstract
-chlorosuccinimide as an inexpensive reagent and proceeds at ambient temperature in high yield within 30 min. The obtained furans serve as exceptionally versatile intermediates and were shown to participate in a series of valuable postmodifications. The fate of the initial sulfonium intermediate was investigated by mechanistic experiments, and computational studies revealed the existence of an unprecedented Pummerer-type rearrangement. The potential for organic synthesis is highlighted by the total synthesis of bisabolene sesquiterpenoids (pleurotins A, B, and D).
Topics & Concepts
ChemistryRegioselectivitySulfoniumReagentYield (engineering)Pummerer rearrangementCombinatorial chemistryRing (chemistry)SulfurOrganic chemistryCatalysisAcetic anhydrideMetallurgySalt (chemistry)Materials scienceSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions