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

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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.
  • Keywords: Beta unsaturated ketones, Carbon, Cyclohexenones, Asymmetric synthesis, Addition reactions, Enantioselective construction, Alder reactions, Quaternary stereocenters, Mannich reactions, Alpha, Michael
  • This is the publisher’s final pdf. The published article is copyrighted by the Royal Society of Chemistry.
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  • 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.
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  • 10
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  • 25
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  • 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.
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