2026-09-19T15:57:01Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/409732022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Gregory C. Fu.
Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2008-03-27T18:32:56Z
2008-03-27T18:32:56Z
2007
2007
http://hdl.handle.net/1721.1/40973
213296828
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007.
Vita.
Includes bibliographical references.
Chapter 1 describes the development of an asymmetric nucleophile-catalyzed [2+2] cycloaddition of ketenes with aldehydes. This is the first report of a catalytic enantioselective synthesis of trisubstituted [beta]-lactones. Two enantioselective phosphine-catalyzed [3+2] cycloadditions of allenoates are detailed in Chapter 2. A method for the asymmetric synthesis of cyclopentenes via a [3+2] cycloaddition of allenoates with enones is first discussed. This is followed by a report of our efforts to extend this [3+2] methodology to imine electrophiles. We conclude, in Chapter 3, with an account of the development of a novel phosphine-catalyzed synthesis of bicyclo[3.3.0]octanones and bicyclo[4.3.0]nonanones. Preliminary results for an enantioselective variant of this method are also disclosed.
by Jonathan E. Wilson.
Ph.D.
345 p.
eng
Massachusetts Institute of Technology
M.I.T. theses are protected by
copyright. They may be viewed from this source for any purpose, but
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http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Enantioselective nucleophile-catalyzed cycloadditions
Thesis
application/pdf
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Publication
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<Abstract>Chapter 1 describes the development of an asymmetric nucleophile-catalyzed [2+2] cycloaddition of ketenes with aldehydes. This is the first report of a catalytic enantioselective synthesis of trisubstituted [beta]-lactones. Two enantioselective phosphine-catalyzed [3+2] cycloadditions of allenoates are detailed in Chapter 2. A method for the asymmetric synthesis of cyclopentenes via a [3+2] cycloaddition of allenoates with enones is first discussed. This is followed by a report of our efforts to extend this [3+2] methodology to imine electrophiles. We conclude, in Chapter 3, with an account of the development of a novel phosphine-catalyzed synthesis of bicyclo[3.3.0]octanones and bicyclo[4.3.0]nonanones. Preliminary results for an enantioselective variant of this method are also disclosed.</Abstract>
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