Asymmetric Syntheses With (-)-Sparteine-Complexed Benzylic and Allylic Organolithium Reagents
Lim, Sung Hyun
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https://hdl.handle.net/2142/84084
Description
Title
Asymmetric Syntheses With (-)-Sparteine-Complexed Benzylic and Allylic Organolithium Reagents
Author(s)
Lim, Sung Hyun
Issue Date
2002
Doctoral Committee Chair(s)
Beak, Peter
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
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.
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