One-Pot Synthesis of Functionalized 2,5-Dihydrofurans via an Amine-Promoted Petasis Borono–Mannich Reaction

A series of functionalized 2,5-dihydrofurans were efficiently synthesized via an amine-promoted Petasis borono–Mannich reaction of 4-substituted 1,2-oxaborol-2(5H)-ols with salicylaldehydes in high yields. The process, which combines a boronic acid-based Mannich reaction and a highly efficient intra...

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Bibliographic Details
Published in:Organic letters 2013-12, Vol.15 (23), p.5944-5947
Main Authors: Cui, Chun-Xiao, Li, Hui, Yang, Xian-Jin, Yang, Jun, Li, Xiao-Qiang
Format: Article
Language:English
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Summary:A series of functionalized 2,5-dihydrofurans were efficiently synthesized via an amine-promoted Petasis borono–Mannich reaction of 4-substituted 1,2-oxaborol-2(5H)-ols with salicylaldehydes in high yields. The process, which combines a boronic acid-based Mannich reaction and a highly efficient intramolecular SN2 cyclization, provides a one-step and efficient route toward 2,5-dihydrofurans from simple and stable starting materials.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402782f