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Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement

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Title Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement
 
Creator GOPI, E
NAMBOOTHIRI, INN
 
Subject CONTAINING NATURAL-PRODUCTS
GEM-DIHALOCYCLOPROPANES
ORGANIC-SYNTHESIS
ELECTROPHILIC CYCLIZATION
BUILDING-BLOCKS
SUBSTITUTED FURANS
HETEROCYCLES
DERIVATIVES
KETONES
CYCLOPROPANATION
 
Description A convenient two-step sequence for the conversion of alkylidenecycloalkanones to bromofurans is reported. The steps involve Mg-mediated diastereoselective dibromocyclopropanation of alkylidenecycloalkanone followed by acidic alumina-mediated regioselective ring expansion of the cyclopropyl ketone. The scope of the reaction was investigated using alkylidenecycloalkanones derived from tetralone, indanone, and benzosuberone to afford 2-aryl-3-bromofurans fused to various benzocycloalkanes. Representative examples of stereoconvergent dibromocyclopropanation and total aromatization of the furobenzocycloalkane are also reported.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-16T13:26:29Z
2014-10-16T13:26:29Z
2013
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 78(3)910-919
http://dx.doi.org/10.1021/jo3022988
http://dspace.library.iitb.ac.in/jspui/handle/100/15662
 
Language en