Two‐Step Sequence Multicomponent Synthesis/Reductive Rearrangement of 2‐Acyl‐2, 3‐dihydrofurans for Modular Assembly of Annulated 4H‐Pyrans. Issue 15 (9th July 2021)

• Record Type: Journal Article
• Authors: Demidov, Maxim R.; Osipov, Dmitry V.; Korol'kov, Konstantin A.; Osyanin, Vitaly A.
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 15(2021)
• Page Start: 3737
• Page End: 3743
• Publication Date: 2021-07-09
• Subjects: Reductive rearrangement -- 4H-Pyrans -- Samarium powder -- Zirconium tetrachloride -- [1, 2]-Aroxyl shift, Zinc; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100261
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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/ZrCl4 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/ZrCl4 redox system. Abstract :