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Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity

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dc.creator Yang, Hua
dc.creator Banerjee, Somdev
dc.creator Carter, Rich G.
dc.date.accessioned 2012-08-06T16:34:28Z
dc.date.available 2013-10-15T22:18:23Z
dc.date.issued 2012-07-07
dc.identifier.citation Yang, H., Banerjee, S., & Carter, R. G. (2012). Proline sulphonamide-catalysed yamada-otani condensation: Reaction development, substrate scope and scaffold reactivity. Organic & Biomolecular Chemistry, 10(25), 4851. en_US
dc.identifier.uri http://hdl.handle.net/1957/31866
dc.description This is the publisher’s final pdf. The published article is copyrighted by The Royal Society of Chemistry and can be found at: www.rsc.org/obc. en_US
dc.description.abstract The development of a proline sulphonamide-catalysed method for enantioselective and diastereoselective construction of functionalized cyclohexenones is described. Impact of catalyst structure as well as solvent effects and additives are explored. A significant substrate scope is demonstrated by variation of both the aldehyde and the enone components. Diastereoselective derivatization of the cyclohexenone scaffold illustrates its utility as a building block for chemical synthesis. en_US
dc.description.sponsorship Financial support was provided by the Oregon State University (OSU) Venture Fund and the National Science Foundation (CHE-0848704). The National Science Foundation (CHE-0722319) and the Murdock Charitable Trust (2005265) are acknowledged for their support of the NMR facility. en_US
dc.language.iso en_US en_US
dc.publisher The Royal Society of Chemistry en_US
dc.relation.ispartofseries Organic & Biomolecular Chemistry en_US
dc.relation.ispartofseries Vol. 10 no. 25 en_US
dc.subject Alpha en_US
dc.subject Beta unsaturated ketones en_US
dc.subject Enantioselective construction en_US
dc.subject Quaternary stereocenters en_US
dc.subject Asymmetric synthesis en_US
dc.subject Addition reactions en_US
dc.subject Mannich reactions en_US
dc.subject Alder reactions en_US
dc.subject Michael en_US
dc.subject Carbon en_US
dc.subject Cyclohexenones en_US
dc.title Proline sulphonamide-catalysed Yamada–Otani condensation: reaction development, substrate scope and scaffold reactivity en_US
dc.type Article en_US
dc.identifier.doi 10.1039/c2ob25400j
dc.description.embargopolicy Repository Administrators en


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