University of Illinois at Urbana-Champaign
The Tandem Inter [4+2]/[3+2] Cycloadditions of Nitroalkenes: The Bridged-Mode
Abstract
dc:descriptionIn continuing investigations, an asymmetric variant of the tandem inter $\lbrack 4 + 2\rbrack$/intra $\lbrack 3 + 2\rbrack$ bridged mode (β-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.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Dixon, Julie Ann
- Contributors dc:contributor
-
- Denmark, Scott E.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI9904433
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84409