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Enantioselective synthesis of substituted indanones from silyloxyallenes. 2010

Jonathan A Brekan, and Troy E Reynolds, and Karl A Scheidt
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, USA.

A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl(2)(PPh(3))(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

UI MeSH Term Description Entries
D007189 Indans Aryl CYCLOPENTANES that are a reduced (protonated) form of INDENES. Indanones
D007192 Indenes A family of fused-ring hydrocarbons isolated from coal tar that act as intermediates in various chemical reactions and are used in the production of coumarone-indene resins.
D000466 Alkadienes Acyclic branched or unbranched hydrocarbons having two carbon-carbon double bonds. Diolefins,Pentadienes
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D017646 Organosilicon Compounds Organic compounds that contain silicon as an integral part of the molecule. Organosilane Compounds,Organosilanes

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