University of Illinois Urbana-Champaign

The Tandem Inter [4+2]/[3+2] Cycloadditions of Nitroalkenes: The Bridged-Mode

Dixon, Julie Ann

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Description

Title
The Tandem Inter [4+2]/[3+2] Cycloadditions of Nitroalkenes: The Bridged-Mode
Author(s)
Dixon, Julie Ann
Issue Date
1998
Doctoral Committee Chair(s)
Denmark, Scott E.
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
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.
Graduation Semester
1998
Type of Resource
text
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http://hdl.handle.net/2142/84409

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