Enantioselective nucleophile-catalyzed cycloadditions
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2008
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| Online Access: | http://hdl.handle.net/1721.1/40973 |
| _version_ | 1826199960416157696 |
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| author | Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology |
| author2 | Gregory C. Fu. |
| author_facet | Gregory C. Fu. Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology |
| author_sort | Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007. |
| first_indexed | 2024-09-23T11:28:34Z |
| format | Thesis |
| id | mit-1721.1/40973 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T11:28:34Z |
| publishDate | 2008 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/409732019-04-10T22:22:21Z Enantioselective nucleophile-catalyzed cycloadditions Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology Gregory C. Fu. Massachusetts Institute of Technology. Dept. of Chemistry. Massachusetts Institute of Technology. Dept. of Chemistry. Chemistry. 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. 2008-03-27T18:32:56Z 2008-03-27T18:32:56Z 2007 2007 Thesis http://hdl.handle.net/1721.1/40973 213296828 eng 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. http://dspace.mit.edu/handle/1721.1/7582 345 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Wilson, Jonathan E., Ph. D. Massachusetts Institute of Technology Enantioselective nucleophile-catalyzed cycloadditions |
| title | Enantioselective nucleophile-catalyzed cycloadditions |
| title_full | Enantioselective nucleophile-catalyzed cycloadditions |
| title_fullStr | Enantioselective nucleophile-catalyzed cycloadditions |
| title_full_unstemmed | Enantioselective nucleophile-catalyzed cycloadditions |
| title_short | Enantioselective nucleophile-catalyzed cycloadditions |
| title_sort | enantioselective nucleophile catalyzed cycloadditions |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/40973 |
| work_keys_str_mv | AT wilsonjonathanephdmassachusettsinstituteoftechnology enantioselectivenucleophilecatalyzedcycloadditions |