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University of Illinois at Urbana-Champaign
Alpha-lithioamine synthetic equivalents from N-Boc secondary amines: Piperideine, pyrrolidine, and perhydroazepine
Abstract
dc:descriptionThe tert-butoxycarbonyl (Boc) group has been shown to be an excellent lithiation directing group for the α\sp\prime-metalation of carbamates from unactivated cyclic secondary amines; piperidine, pyrrolidine, and perhydroazepine to provide α-lithioamine synthetic equivalents. The Boc group can be easily introduced on the nitrogen, stable to strong alkyllithium bases, and easily cleaved after elaborations. Determination of the stereochemistry of the lithiation-substitution sequences and the use of this approach to synthesize representative piperidine alkaloids which have cis-2,6-disubstituents (N-Boc dihydropinidine) and trans-2,6-disubstituents (solenopsin A) in high yields will be presented.
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
- 2011
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Lee, Won Koo
- Contributors dc:contributor
-
- Beak, Peter
Subjects
dc:subject × 1Rights
dc:rights- Statement dc:rights
-
- Copyright 1991 Lee, Won Koo
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
-
AAI9136652
(UMI)AAI9136652 - OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/23412