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Title:The Tandem Inter [4+2]/[3+2] Cycloadditions of Nitroalkenes: The Bridged-Mode
Author(s):Dixon, Julie Ann
Doctoral Committee Chair(s):Denmark, Scott E.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:In continuing investigations, an asymmetric variant of the tandem inter $\lbrack 4 + 2\rbrack$/intra $\lbrack 3 + 2\rbrack$ bridged mode ($\beta$-tether) cycloaddition of nitroalkenes has been developed. This new sequence involves the Lewis-acid-promoted $\lbrack 4 + 2\rbrack$ cycloaddition of a variety of nitro olefins with 1-alkoxy-1,4-pentadienes derived from (1R,2S)-phenylcyclohexanol. Intramolecular $\lbrack 3 + 2\rbrack$ cycloadditions afforded stable nitroso acetals that were reduced using nickel boride to provide enantiomerically enriched aminocyclopentanes in good yields and high enantiomeric excess. Additionally, the Lewis acid employed in the $\lbrack 4 + 2\rbrack$ cycloaddition was found to impart a remarkable influence on the stereochemical outcome of the tandem sequence.
Issue Date:1998
Type:Text
Language:English
Description:279 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1998.
URI:http://hdl.handle.net/2142/84409
Other Identifier(s):(MiAaPQ)AAI9904433
Date Available in IDEALS:2015-09-25
Date Deposited:1998


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