Mechanistic Investigations and Synthetic Development of (-)-Sparteine Mediated Asymmetric Benzylic Lithiation-Substitution Reactions of Secondary Amides
Laumer, Jason Matthew
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https://hdl.handle.net/2142/84057
Description
Title
Mechanistic Investigations and Synthetic Development of (-)-Sparteine Mediated Asymmetric Benzylic Lithiation-Substitution Reactions of Secondary Amides
Author(s)
Laumer, Jason Matthew
Issue Date
2001
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
The synthetic utility of the lithiation-substitutions of N-(2-phenethyl)isobutyramide has also been investigated. Enantioenriched substituted products have been carried forward in the synthesis of 1,4-disubstituted dihydro- and tetrahydroisoquinolines. Variation of either substituent is convenient as the 4-position substituent is determined by choice of the electrophile in the lithiation-substitution and the 1-position substituent is introduced prior to cyclization.
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