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Title:Beta-lithiations of carboxamides: An investigation of the regio- and stereoselectivity of directed lithiations
Author(s):Lutz, Gary Paul
Doctoral Committee Chair(s):Beak, Peter
Department / Program:Chemistry, Organic
Discipline:Chemistry, Organic
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract:An investigation of the diastereoselective $\beta$-metalation and of the structure of a carbanion of a $\beta$-phenyl tertiary amide has been carried out. The directed metalation has been found to occur with high diastereoselectivity and the resulting carbanion is best described as a pyramidal benzyllithium species based on $\sp{13}$C NMR evidence.
Secondary amides have been shown to act as directing groups for $\beta$-lithiations, and the dianion homoenolate equivalents have been shown to react with a variety of electrophiles. We have found that the remote metalations can be directed by secondary amides employing several anion stabilizing groups, and the secondary amides can undergo remote metalations when no $\alpha$-alkyl substituent is present. The rate of the directed deprotonation has been found to be dependent upon the chain length between the amide group and the anion stabilizing group. The investigation of using secondary amides as homoenolate equivalents as well as the potential and limitations of these homoenolate equivalents will be addressed.
Issue Date:1991
Rights Information:Copyright 1991 Lutz, Gary Paul
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9210904
OCLC Identifier:(UMI)AAI9210904

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