Asymmetric Lithiation-Substitution Sequences of Functionalized Allylic and Benzylic Amines Mediated by (-)-Sparteine

Modification of the allyl amine with selected substituents at the beta and gamma-positions allowed for an examination of yields, product distributions, enantioenrichments, mechanistic understanding and synthetic applications. With an extended allyl amine, enantioenriched diene products were obtained which participated in highly selective Diels-Alder cyclizations. Methyl substitution at the beta-position gave a substrate suitable for mechanistic studies. The addition of a heteroaromatic ring on the allyl backbone provided a substrate that behaved very similarly to the cinnamyl analogue. The robust nature of the furan ring was observed as a variety of conditions needed for enecarbamate transformations did not affect the ring stability.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Kim, Dwight D.

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3101882

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84116