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Title:Alpha-lithioamine synthetic equivalents from N-Boc secondary amines: Piperideine, pyrrolidine, and perhydroazepine
Author(s):Lee, Won Koo
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:The tert-butoxycarbonyl (Boc) group has been shown to be an excellent lithiation directing group for the $\alpha\sp\prime$-metalation of carbamates from unactivated cyclic secondary amines; piperidine, pyrrolidine, and perhydroazepine to provide $\alpha$-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.
Issue Date:1991
Type:Text
Language:English
URI:http://hdl.handle.net/2142/23412
Rights Information:Copyright 1991 Lee, Won Koo
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9136652
OCLC Identifier:(UMI)AAI9136652


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