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Title:Enantioselective Alpha-Lithiation of N-Boc-N-(p-Methoxyphenyl)allylamines Mediated by (--)-Sparteine
Author(s):Weisenburger, Gerald Allen
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: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.
Issue Date:1998
Type:Text
Language:English
Description:223 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1998.
URI:http://hdl.handle.net/2142/84433
Other Identifier(s):(MiAaPQ)AAI9912426
Date Available in IDEALS:2015-09-25
Date Deposited:1998


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