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University of Illinois at Urbana-Champaign
Asymmetric Syntheses With (-)-Sparteine-Complexed Benzylic and Allylic Organolithium Reagents
Abstract
dc:descriptionThe kinetic resolution of racemic cyclic unsaturated esters with the organolithium intermediates derived from lithiation of N-Boc- N-(p-methoxyphenyl)cinnamylamine with n -BuLi/(-)-sparteine was investigated. Kinetic resolution in conjugate addition reactions with alpha,beta-unsaturated lactones proceed with retention of configuration to provide 1,4-addition products with three contiguous stereogenic centers with high stereoselectivities. In all cases of a 1,4-addition selectivity factors >20 were obtained, as calculated using the enantiomeric excess of the conjugate addition product.
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
-
- Lim, Sung Hyun
- Contributors dc:contributor
-
- Beak, Peter
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3070370
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84084