ol403035g_si_002.pdf (14.24 MB)
Rhodium(II)-Catalyzed Alkyne Amination of Homopropargylic Sulfamate Esters: Stereoselective Synthesis of Functionalized Norcaradienes by Arene Cyclopropanation
journal contribution
posted on 2014-01-03, 00:00 authored by Ryan A. Brawn, Kaicheng Zhu, James S. PanekA rhodium(II) catalyzed nitrene–alkyne
cycloaddition of
stereochemically well-defined homopropargylic ethers is followed by
arene cyclopropanation to afford unique tetracyclic norcaradiene products
bearing a cyclic sulfamate. Products from the arene cyclopropanation
(Buchner reaction) can be converted to fused cycloheptatrienes via
a ring enlarging electrocyclization after nucleophilic ring opening
of the cyclic sulfamate ester.
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homopropargylicetherNorcaradieneRhodiumnucleophilic ring openingcyclic sulfamate estercycloadditionAminationelectrocyclizationrhodiumSynthesiAreneBuchnerarene cyclopropanationAlkyneHomopropargylic Sulfamate EstersFunctionalizedStereoselectivetetracyclic norcaradiene productsnitrenecycloheptatrienestereochemicallyCyclopropanationA
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