(-)-Sparteine Mediated Lithiation of N-Boc-N-P-(methoxyphenyl) Allylic Amines and Conjugate Addition to Nitroalkenes: Scope, Reaction Pathway, and Synthetic Applications
Johnson, Timothy Allen
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https://hdl.handle.net/2142/84080
Description
Title
(-)-Sparteine Mediated Lithiation of N-Boc-N-P-(methoxyphenyl) Allylic Amines and Conjugate Addition to Nitroalkenes: Scope, Reaction Pathway, and Synthetic Applications
Author(s)
Johnson, Timothy Allen
Issue Date
2002
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 enecarbamate products of the conjugate additions may also be easily elaborated to enantioenriched functionalized cyclopentanoids. Hydrolysis of the enecarbamates followed by intramolecular nitro-aldol cyclization and dehydration provides substituted nitrocyclopentenes that were converted to substituted cyclopentanones and cyclopentylamines.
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