Date of Award
1999
Publication Type
Master Thesis
Degree Name
M.Sc.
Department
Chemistry and Biochemistry
Keywords
Chemistry, Organic.
Supervisor
McIntosh, John M.,
Rights
info:eu-repo/semantics/openAccess
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
Abstract
Part A. The alkylation trans 2-arylcyclohexyl hippurates with a series of electrophiles was examined. The reaction stereoselectivity varied from 46 to 81% depending on the steric and electronic nature of the electrophile when (Ar = phenyl). Higher stereoselectivity was observed when reacting electrophiles of increasing pi-character. When the chiral auxiliary contained a naphthyl group the stereoselectivity was >80% for every electrophile used. Part B. The alkylation of the trans 2-phenylcyclohexylamide of methyl glycinate with a series of electrophiles was examined. Incorporation of the chiral auxiliary on the amino terminus of the amino acid appears to induce good stereoselectivity only when the electrophiles contain a point of unsaturation. The reaction stereoselectivity ranged from 21 to 80% depending on the electronic nature of the electrophiles. It is proposed that a pi-stacking interaction between the aromatic group on the auxiliary and the unsaturated electrophiles was responsible for the high stereochemical excess observed. Source: Masters Abstracts International, Volume: 39-02, page: 0514. Adviser: John M. McIntosh. Thesis (M.Sc.)--University of Windsor (Canada), 1999.
Recommended Citation
Peters, Scott Owen., "Induced pi-facial discrimination in the alkylation of chiral derivatives of glycine." (1999). Electronic Theses and Dissertations. 2426.
https://scholar.uwindsor.ca/etd/2426