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Title:Asymmetric Lithiation-Substitution Sequences of Functionalized Allylic and Benzylic Amines Mediated by (-)-Sparteine
Author(s):Kim, Dwight D.
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: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.
Issue Date:2003
Type:Text
Language:English
Description:177 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003.
URI:http://hdl.handle.net/2142/84116
Other Identifier(s):(MiAaPQ)AAI3101882
Date Available in IDEALS:2015-09-25
Date Deposited:2003


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