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Templated Carbene Metathesis Reactions from the Modular Assembly of Enol‐diazo Compounds and Propargyl Acetates
Author(s) -
Qian Yu,
Shanahan Charles S.,
Doyle Michael P.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301000
Subject(s) - diazo , chemistry , enol , carbene , propargyl , nucleophile , metathesis , cascade reaction , salt metathesis reaction , cyclopropanation , lewis acids and bases , coupling reaction , organic chemistry , combinatorial chemistry , catalysis , polymerization , polymer
A Lewis acid mediated coupling reaction of enol‐diazo nucleophiles and propargyl acetates has provided rapid and diverse access to complex alkynyl‐tethered diazocarbonyl compounds. The ability of the coupling reaction to vary critical functionality flanking the diazo group was explored as a way to direct the outcome of a series of metal‐catalyzed carbene metathesis cascade reactions. These cascade reactions provided diverse, biologically interesting carbocyclic and heterocyclic compounds in only a few steps from readily available materials.