Induced pi-facial discrimination in the alkylation of chiral derivatives of glycine.

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.

Name thesis:degree_name

M.Sc.

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Chemistry and Biochemistry

Grantor

University of Windsor

Year dc:date.issued

1999

Author dc:creator

• Peters, Scott Owen.

Advisor dc:contributor.advisor

• McIntosh, John M.,

Licence

• http://creativecommons.org/licenses/by-nc-nd/4.0/

Language dc:language.iso

en_CA

Handle dc:identifier.uri

https://hdl.handle.net/20.500.14776/2062

OAI identifier oai:identifier

oai:uwindsor.scholaris.ca:20.500.14776/2062