Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines

The lithiation-substitution of N-Boc benzylamines and cyclopropylamines have been investigated to explore the synthetic potential of these substrates. We have achieved the syntheses of highly enantioenriched benzylic α-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary α-substituted benzylamines and α,α-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the α and β lithiation-substitution of cyclopropanes. Extension of this chemistry to syntheses of highly functionalized cyclopentane by (3 + 2) cycloaddition and asymmetric synthesis of N-Boc azabicyclic (3.10) hexane was investigated.

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

• Park, Yong Sun

Contributors dc:contributor

• Beak, Peter

• Chemistry, Organic

Statement dc:rights

• Copyright 1996 Park, Yong Sun

Language dc:language

eng

Identifier

9780591089622
AAI9702635
(UMI)AAI9702635

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/19974