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Title:Novel syntheses by directed lithiations of N-Boc benzylamines and cyclopropylamines
Author(s):Park, Yong Sun
Doctoral Committee Chair(s):Beak, Peter
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract: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 $\alpha$-substituted N-Boc secondary amines using RLi/(-)-sparteine. Extension of this chemistry to asymmetric syntheses of both enantiomers of primary $\alpha$-substituted benzylamines and $\alpha,\alpha$-disubstituted benzylamines has been achieved successfully. Also, the N-Boc group was used as an activating and directing group for the $\alpha$ and $\beta$ 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.
Issue Date:1996
Type:Text
Language:English
URI:http://hdl.handle.net/2142/19974
ISBN:9780591089622
Rights Information:Copyright 1996 Park, Yong Sun
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9702635
OCLC Identifier:(UMI)AAI9702635


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