A Domino Strategy for the Synthesis of 2H‐Pyrans from Propargyl Vinyl Ethers

Stable monocyclic 2H‐pyrans are synthesized from readily available tertiary propargyl vinyl ethers via a metal‐free all‐pericyclic domino manifold involving a sequential propargyl Claisen rearrangement/[1,3]H‐shift/oxa‐6π electrocyclization set of reactions. The wide scope of this protocol is exempl...

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Bibliographic Details
Authors: Tejedor, David, Delgado-Hernández, Samuel, Diana-Rivero, Raquel, Díaz-Díaz, Abián, García-Tellado, Fernando
Format: article
Status:Versión aceptada para publicación
Publication Date:2019
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/176748
Online Access:http://hdl.handle.net/10261/176748
Access Level:Open access
Keyword:2H‐Dihydropyran
Propargyl vinyl ethers
Domino reactions
Pericyclic reactions
Organocatalysis
Description
Summary:Stable monocyclic 2H‐pyrans are synthesized from readily available tertiary propargyl vinyl ethers via a metal‐free all‐pericyclic domino manifold involving a sequential propargyl Claisen rearrangement/[1,3]H‐shift/oxa‐6π electrocyclization set of reactions. The wide scope of this protocol is exemplified by the synthesis of 21 different 2H‐pyrans incorporating a varied substitution pattern at the ring.

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