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Improved synthesis and application of planar-chiral nucleophilic catalysts in asymmetric reactions and copper-catalyzed enantioselective N-H insertion reactions

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dc.contributor.advisor Gregory C. Fu. en_US
dc.contributor.author Lee, Elaine C en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.date.accessioned 2007-12-07T16:16:53Z
dc.date.available 2007-12-07T16:16:53Z
dc.date.copyright 2007 en_US
dc.date.issued 2007 en_US
dc.identifier.uri http://hdl.handle.net/1721.1/39741
dc.description Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007. en_US
dc.description Vita. en_US
dc.description Includes bibliographical references. en_US
dc.description.abstract The development of an improved synthesis of nucleophilic planar-chiral catalysts is described in Chapter 1. This route is amenable to scale-up and preparative chiral HPLC is unnecessary to resolve the racemic catalysts. Using planar-chiral catalysts, two synthetic methodology projects have been developed: Chapter 2 describes the first asymmetric synthesis of trans P-lactams, and Chapter 3 describes the asymmetric synthesis of tertiary a-chloroesters. In the chapter describing the asymmetric synthesis of trans [beta]-lactams, we present mechanistic data supporting a novel mechanism, in which the N-triflylimine, rather than the ketene, reacts with the catalyst first. In the chapter describing the asymmetric synthesis of tertiary a-chloroesters, we introduced an under-utilized commercially available chlorinating reagent (2,2,6,6-tetrachlorocyclohexanone). Finally, in chapter 4, the Cu-catalyzed asymmetric synthesis of [alpha]-aminoesters via an N-H insertion is described. We have demonstrated that carbamates such as BocNH2 and CbzNH2 are efficient coupling partners in reactions with a-diazoesters to generate highly useful Boc- or Cbz-protected a-aminoesters. en_US
dc.description.statementofresponsibility by Elaine C. Lee. en_US
dc.format.extent 215 p. en_US
dc.language.iso eng en_US
dc.publisher Massachusetts Institute of Technology en_US
dc.rights M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. en_US
dc.rights.uri http://dspace.mit.edu/handle/1721.1/7582
dc.subject Chemistry. en_US
dc.title Improved synthesis and application of planar-chiral nucleophilic catalysts in asymmetric reactions and copper-catalyzed enantioselective N-H insertion reactions en_US
dc.title.alternative Copper-catalyzed enantioselective N-H insertion reactions en_US
dc.type Thesis en_US
dc.description.degree Ph.D. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.identifier.oclc 181376081 en_US


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