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Lewis Acid‐Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4‐Hydroxy‐2 H ‐chromen‐2‐ones
Author(s) -
Han YaPing,
Li XueSong,
Li Ming,
Zhu XinYu,
Liang YongMin
Publication year - 2018
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.201800131
Subject(s) - chemistry , annulation , lewis acids and bases , catalysis , formal synthesis , combinatorial chemistry , functional group , organic chemistry , stereochemistry , polymer
A Lewis acid‐catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2‐c]chromen‐5(2 H )‐one fragments has been developed using propargylic alcohols and 4‐hydroxy‐2 H ‐chromen‐2‐ones as the substrates. The protocol provides a one‐step, environmentally benign method of accessing a broad range of pyrano[3,2‐c]chromen‐5(2 H )‐one derivatives in excellent yields under mild conditions and with good functional‐group tolerance. The method is effective on the gram scale, which highlights the inherent practicality of this synthetic transformation.