Enantioselective Alpha-Lithiation of N-Boc-N-(p-Methoxyphenyl)allylamines Mediated by (--)-Sparteine
Weisenburger, Gerald Allen
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https://hdl.handle.net/2142/84433
Description
Title
Enantioselective Alpha-Lithiation of N-Boc-N-(p-Methoxyphenyl)allylamines Mediated by (--)-Sparteine
Author(s)
Weisenburger, Gerald Allen
Issue Date
1998
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
Tin-lithium exchange of enantioenriched allylic stannanes in the presence of (-)-sparteine followed by electrophilic substitution provides enecarbamates with configurations opposite to that obtained by the deprotonation sequence. The enecarbamates can be hydrolyzed to aldehydes or reduced to amines, and therefore provide facile entry into chiral homoenolate synthetic equivalents and chiral gamma-lithioamine synthetic equivalents.
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