Asymmetric Lithiation-Substitution Sequences of Functionalized Allylic and Benzylic Amines Mediated by (-)-Sparteine
Kim, Dwight D.
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https://hdl.handle.net/2142/84116
Description
Title
Asymmetric Lithiation-Substitution Sequences of Functionalized Allylic and Benzylic Amines Mediated by (-)-Sparteine
Author(s)
Kim, Dwight D.
Issue Date
2003
Doctoral Committee Chair(s)
Beak, Peter
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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.
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