Alpha-lithioamine synthetic equivalents from N-Boc secondary amines: Piperideine, pyrrolidine, and perhydroazepine
Lee, Won Koo
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https://hdl.handle.net/2142/23412
Description
Title
Alpha-lithioamine synthetic equivalents from N-Boc secondary amines: Piperideine, pyrrolidine, and perhydroazepine
Author(s)
Lee, Won Koo
Issue Date
1991
Doctoral Committee Chair(s)
Beak, Peter
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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.
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