Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 15, Pages 7321-7332Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01106
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Funding
- MINECO [CTQ2013-42106-P, SEV-2013-0319]
- European Research Council [321066]
- AGAUR [2014 SGR 818]
- ICIQ Foundation
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Cycloisomerizations of 1,n-enynes catalyzed by gold(I) proceed via electrophilic species with a highly distorted cyclopropyl gold(I) carbene-like structure, which can react with different nudeophiles to form a wide variety of products by attack at the cyclopropane or the carbene carbons. Particularly important are reactions in which the gold(I) carbene reacts with alkenes to form cyclopropanes either intra- or intermolecularly. In the absence of nudeophiles, 1,n-enynes lead to a variety of cycloisomerized products including those resulting from skeletal rearrangements. Reactions proceeding through cyclopropyl gold(I) carbene-like intermediates are ideally suited for the bioinspired synthesis of terpenoid natural products by the selective activation of the alkyne in highly functionalized enynes or polyenynes.
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