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Title:Asymmetric Syntheses With (-)-Sparteine-Complexed Benzylic and Allylic Organolithium Reagents
Author(s):Lim, Sung Hyun
Doctoral Committee Chair(s):Beak, Peter
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The 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.
Issue Date:2002
Type:Text
Language:English
Description:209 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2002.
URI:http://hdl.handle.net/2142/84084
Other Identifier(s):(MiAaPQ)AAI3070370
Date Available in IDEALS:2015-09-25
Date Deposited:2002


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