Micelle‐Mediated Trimerization of Ynals to Orthogonally Substituted 4<i>H</i>‐Pyrans in Water: Downstream Rearrangement to Bioactive 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐diene Frameworks
Showkat Rashid, Bilal A. Bhat, Goverdhan Mehta
Abstract
Abstract An efficient trimerization of ynals to diversely substituted 4 H ‐pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid‐mediated downstream rearrangement of the derived 4 H ‐pyrans to interesting 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐dienes has been observed.
Topics & Concepts
ChemistryMicelleCatalysisPulmonary surfactantPyranProton NMROrganic chemistryDieneMedicinal chemistryStereochemistryAqueous solutionBiochemistryNatural rubberCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions