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Synthesis of ( E )‐α,β‐Unsaturated Carbonyls via Silver‐Catalyzed Tandem Epoxide Rearrangement/Intermolecular Carbonyl‐ Heteroalkyne Metathesis
Author(s) -
Zhu Hui,
Jin Weiwei,
He Jiayao,
Zhang Yan,
Zhu Gangguo
Publication year - 2016
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.201600623
Subject(s) - chemistry , metathesis , epoxide , stereoselectivity , tandem , intermolecular force , catalysis , salt metathesis reaction , stereochemistry , organic chemistry , molecule , polymerization , polymer , materials science , composite material
A regio‐ and stereoselective method for the synthesis of ( E )‐α,β‐unsaturated carbonyls has been developed v ia a silver‐catalyzed tandem epoxide rearrangement/intermolecular carbonyl‐heteroalkyne metathesis. Various heteroalkynes including ynol ethers, ynamides, and thioalkynes work well for this transformation, leading to the production of ( E )‐α,β‐unsaturated esters, amides, and thioesters in moderate to excellent yields with good functional group compatibility. It represents one of the rare examples of regio‐ and stereoselective intermolecular alkyne‐carbonyl metathesis (ACM).