Mechanistic studies of asymmetric induction at benzylic centers of organolithium species

The mechanisms of asymmetric induction involving the lithiation and substitution of N-benzyl-N-Boc-N-p-methodically amine and N-benzyl-N-Boc-N-3-chloropropyl amine were investigated and are reported here. These two substrates undergo deprotonation with butyllithium in the presence of the chiral ligand (${-}$)-sparteine to generate their benzyllithium intermediates, which are subsequently reacted with electrophiles to yield highly enantioenriched products. For N-benzyl-N-Boc-N-3-chloropropyl amine, the electrophile is a part of the substrate, so the reaction is an intramolecular cyclization.

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

2011

Author dc:creator

• Lee, Steven Paul

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Statement dc:rights

• Copyright 1996 Lee, Steven Paul

Language dc:language

eng

Identifier

9780591198782
AAI9712346
(UMI)AAI9712346

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/19584