Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.247901
Title: Development and synthetic applications of the asymmetric anionic amino-Cope rearrangement
Author: Baird, Robert Duncan
ISNI:       0000 0001 3437 8376
Awarding Body: Loughborough University
Current Institution: Loughborough University
Date of Award: 1996
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Abstract:
The thermal and anionic amino-Cope rearrangement of suitably functionalised 3-amino-1,5-hexadienes could potentially constitute a powerful tool for the stereoselective synthesis of highly functionalised acyclic or cyclic systems. [Illustration omitted.] Incorporation of β-aminoalcohol auxiliaries into the diene enabled high diastereoselectivity to be obtained during the 1,2-addition of the allyl Grignard reagent to α,β-unsaturated imines. Asymmetric anionic amino-Cope rearrangement of the diastereoisomerically pure 3-amino-1,5-diene substrates furnished the target aldehyde in good yield and with high levels of asymmetric induction (up to 94% e.e.). The aldehyde obtained was used as a non-racemic starting material to synthesise small heterocycles, with high levels of diastereoselectivity in some cases, providing a high yielding route to some important chiral building blocks. The successful formation of both tetrahydropyrans and lactones without any apparent loss of chirality was achieved and provided a background for investigation into the synthesis of piperidines, which could lead to a plausible route to biologically significant aza-sugars.
Supervisor: Not available Sponsor: EPSRC
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.247901  DOI: Not available
Keywords: Amino hexadienes
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