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University of Illinois at Urbana-Champaign
Enantioselective Alpha-Lithiation of N-Boc-N-(p-Methoxyphenyl)allylamines Mediated by (--)-Sparteine
Abstract
dc:descriptionTin-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.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Weisenburger, Gerald Allen
- Contributors dc:contributor
-
- Beak, Peter
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI9912426
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84433