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      Non-felkin diastereoselectivity in aldol couplings of thiopyran-based polypropionate synthons

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      NikkiTheaker2009.pdf (2.913Mb)
      Date
      2009-12
      Author
      Theaker, Nikki E.
      Type
      Thesis
      Degree Level
      Masters
      Metadata
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      Abstract
      Polypropionates represent a large family of natural products and several strategies have been developed for their synthesis. The aldol reaction is one of the most important tools for the construction of polypropionate natural products. The Ward group has developed an approach to polypropionate natural products based on sequential aldol reactions of thiopyran building blocks. The Thiopyran Route to Polypropionates (TR2P) involves the stepwise aldol reactions of 15 and 16 to rapidly access stereochemically complex tetrapropionate and hexapropionate synthons in a few steps. The current work describes the effort to prepare enantioenriched 17-AA and/or 17-SA through chiral transition metal based Lewis acids (176) and chiral organocatalysts (48, 179) with chelating Lewis acids. The preparation of non-Felkin tetrapropionate and hexapropionate synthons through the use of a weak base in conjunction with a Lewis acid was developed.
      Degree
      Master of Science (M.Sc.)
      Department
      Chemistry
      Program
      Chemistry
      Supervisor
      Ward, Dale E.
      Committee
      Dimmock, J. R.; Gravel, Michel
      Copyright Date
      December 2009
      URI
      http://hdl.handle.net/10388/etd-12242009-105241
      Subject
      soft enolization
      direct aldol
      non-Felkin addition
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      • Graduate Theses and Dissertations
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