New approaches for the stereoselective synthesis of N-heterocycles

Daly, Mark (2012) New approaches for the stereoselective synthesis of N-heterocycles. PhD thesis, University of Glasgow.

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Abstract

A stereoselective approach has been developed for the flexible synthesis of substituted 2-pyrrolidones and 2-piperidones. By employing the key Overman rearrangement, efficient transfer of stereochemistry was achieved, and an acylation and ring closing metathesis strategy afforded a library of target N-heterocycles. In addition, the optimisation of a synthesis of 4-oxopipecolic acid derivatives from L-aspartic acid was investigated. A novel, milder and higher yielding 6-endo-trig cyclisation procedure was developed. This allowed for the generation of a library of 2,6-cis-substituted 4-oxopipecolic derivatives. Stereoselective carbonyl reduction extended the synthesis further to include 4-hydroxypipecolic acid derivatives.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: organic, synthesis, stereoselective, heterocycle, overman, rearrangement, metathesis, cyclisation, pyrrolidones, piperidones, lactam, pipecolic, quaternary, claisen
Subjects: Q Science > QD Chemistry
Colleges/Schools: College of Science and Engineering > School of Chemistry
Funder's Name: UNSPECIFIED
Supervisor's Name: Sutherland, Dr. Andrew
Date of Award: 2012
Depositing User: Mr Mark Daly
Unique ID: glathesis:2012-3807
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 21 Dec 2012 15:52
Last Modified: 06 Jun 2013 07:33
URI: http://theses.gla.ac.uk/id/eprint/3807

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