Two‐Step Sequence Multicomponent Synthesis/Reductive Rearrangement of 2‐Acyl‐2,3‐dihydrofurans for Modular Assembly of Annulated 4 H ‐Pyrans | Zendy

Demidov Maxim R. | Zendy; Osipov Dmitry V. | Zendy; Korol'kov Konstantin A. | Zendy; Osyanin Vitaly A. | Zendy

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Two‐Step Sequence Multicomponent Synthesis/Reductive Rearrangement of 2‐Acyl‐2,3‐dihydrofurans for Modular Assembly of Annulated 4 H ‐Pyrans

Author(s) -

Demidov Maxim R.,

Osipov Dmitry V.,

Korol'kov Konstantin A.,

Osyanin Vitaly A.

Publication year - 2021

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202100261

Subject(s) - chemistry , redox , sequence (biology) , carbene , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry

A variety of trans ‐2‐acyl‐2,3‐dihydrofurans have been assembled from readily available structurally diverse precursors and then rearranged into a series of annulated 4 H ‐pyrans by the action of Sm/TMSCl or Zn/ZrCl 4 redox systems. Present synthetic sequence is claimed as a modular approach to hetero‐ and carbon‐fused 4 H ‐pyrans. The rearrangement involves the SET reduction of carbonyl group to carbene followed by rare type of [1,2]‐aroxyl shift. Synthetic toolbar was enriched with the use of the Zn/ZrCl 4 redox system.

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