A Domino Strategy for the Synthesis of 2H‐Pyrans from Propargyl Vinyl Ethers. Issue 8 (11th February 2019)

• Record Type: Journal Article
• Authors: Tejedor, David; Delgado‐Hernández, Samuel; Diana‐Rivero, Raquel; Díaz‐Díaz, Abián; García‐Tellado, Fernando
• Is Part Of: European journal of organic chemistry. Issue 8(2019)
• Page Start: 1784
• Page End: 1790
• Publication Date: 2019-02-11
• Subjects: 2H‐Dihydropyran -- Propargyl vinyl ethers -- Domino reactions -- Pericyclic reactions -- Organocatalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801847
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Stable monocyclic 2 H ‐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 2 H ‐pyrans incorporating a varied substitution pattern at the ring. Abstract : Simple and direct : an all‐pericyclic domino manifold transforms propargyl vinyl ethers into 2H‐pyrans through a sequential propargyl Claisen rearrangement/[1, 3]H‐shift/oxa‐6π electrocyclization. The wide scope of this protocol is exemplified by the synthesis of 21 different 2 H ‐pyrans incorporating a varied substitution pattern at the ring.