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Alpha-lithioamine synthetic equivalents from N-Boc secondary amines: Piperideine, pyrrolidine, and perhydroazepine

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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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