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Brønsted Acid Catalyzed Cycloisomerizations of 5,2‐Enyne‐1‐ones: Highly Regioselective Synthesis of 2,3‐Dihydro‐4 H ‐pyran‐4‐ones
Author(s) -
Yang Fang,
Ji KeGong,
Zhao ShuChun,
Ali Shaukat,
Ye YuYing,
Liu XueYuan,
Liang YongMin
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103771
Subject(s) - enyne , regioselectivity , cycloisomerization , catalysis , alkene , pyran , chemistry , propargyl , brønsted–lowry acid–base theory , stereochemistry , combinatorial chemistry , organic chemistry
Dual‐action catalyst : A Brønsted acid catalyzed regioselective cycloisomerization was found to be highly effective for the preparation of structurally diverse 2,3‐dihydro‐4 H ‐pyran‐4‐ones in a 6‐ exo ‐trig manner from the corresponding 5,2‐enyne‐1‐ones. In this reaction, the Brønsted acid acts as a dual catalyst activating both the carbonyl and alkene moieties in a cascade manner (see scheme).