Digital Repository

Design and synthesis of new monoterpenoid derived ligands for asymmetric catalysis /

DSpace/Manakin Repository

Show simple item record

dc.contributor.author Millar, Monte J. en_US
dc.date.accessioned 2009-05-21T12:53:14Z
dc.date.available 2009-05-21T12:53:14Z
dc.date.issued 1999-05-21T12:53:14Z
dc.identifier.uri http://hdl.handle.net/10464/1242
dc.description.abstract The work to be presented herein illustrates several important facts. First, the synthesis of BIBOL (19), a 1,4-diol derived from the monoterpene camphor has allowed us to demonstrate that oxidative dimerizations of enolates can, and do proceed with nearly complete diastereoselectivity under kinetically controlled conditions. The yield of BIBOL is now 50% on average, with a 10% yield of a second diastereomer, which is likely the result of a non-kinetic hydride reduction, thereby affording the epimeric alcohol, 20, coupled on the exo face of camphor. This implies the production of 60% of a single coupling diastereomer. No other diastereomers from the reduction were observed. The utility of BEBOL has been illustrated in early asymmetric additions of diethylzinc to aryl aldehydes, with e.e.'s as high as 25-30%. '^' To further the oxidative coupling work, the same methodology which gave rise to BIBOL was applied to the chiral pool ketone, menthone. Interestingly, this gave an excellent yield of the a-halohydrin (31), which is the result of a chlorination of menthone. This result clearly indicates the high stereoselectivity of the process regardless of the outcome, and has illustrated an interesting dichotomy between camphor and menthone. The utility of the chlorination product as a precursor other chiral ligands is currently being investigated. > ' Finally, a new series of 1,3-diols as well as a new aminoalcohol have successfully been synthesized from highly diastereoselective aldol/mannich reactions. Early studies have indicated their potential in asymmetric catalysis, while employing pi-stack interactions as a means of controlling enantioselective aldol reactions. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Asymmetric synthesis. en_US
dc.subject Catalysis. en_US
dc.subject Ligands. en_US
dc.subject Monoterpenes. en_US
dc.subject Alcohols. en_US
dc.title Design and synthesis of new monoterpenoid derived ligands for asymmetric catalysis / en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name M.Sc. Chemistry en_US
dc.degree.level Masters en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


Files in this item

This item appears in the following Collection(s)

Show simple item record

Search The Repository


Browse

My Account

Statistics


About the Digital Repository