Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2009.
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| 格式: | Thesis |
| 语言: | eng |
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Massachusetts Institute of Technology
2009
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| 在线阅读: | http://hdl.handle.net/1721.1/49745 |
| _version_ | 1826198286873133056 |
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| author | Smith, Sean W. (Sean Wesley) |
| author2 | Gregory C. Fu. |
| author_facet | Gregory C. Fu. Smith, Sean W. (Sean Wesley) |
| author_sort | Smith, Sean W. (Sean Wesley) |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2009. |
| first_indexed | 2024-09-23T11:02:30Z |
| format | Thesis |
| id | mit-1721.1/49745 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T11:02:30Z |
| publishDate | 2009 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/497452019-04-10T12:52:21Z Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides Smith, Sean W. (Sean Wesley) 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, 2009. Vita. Includes bibliographical references. Chapter 1 describes the development of two organocatalytic processes. The first is a 13-alkylation reaction of Michael acceptors, and represents a novel umpolung process catalyzed by N-heterocyclic carbenes. The second section discusses the first successful phosphine-catalyzed, y-alkylation reaction of isomerizable allenoates. A highly enantioselective variant of this reaction is described. Chapter 2 discusses nickel-catalyzed cross-coupling reactions of secondary propargylic halides with a variety of organozinc nucleophiles. Section 2.2 describes progress toward an asymmetric alkylation reaction. In Section 2.3, the development of the first alkyl-alkyl secondary-secondary cross-coupling is described; Section 2.4 describes the application of this coupling reaction to the formal synthesis of a-cembra-2,7,1 1-triene-4,6-diol. The last section of this thesis (Section 2.5) discusses the development of the first asymmetric Negishi reaction of arylzinc reagents with secondary electrophiles. by Sean W. Smith. Ph.D. 2009-11-06T16:28:46Z 2009-11-06T16:28:46Z 2009 2009 Thesis http://hdl.handle.net/1721.1/49745 455436301 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 353 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Smith, Sean W. (Sean Wesley) Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title | Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title_full | Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title_fullStr | Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title_full_unstemmed | Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title_short | Progress in nucleophilic catalysis and development of nickel-catalyzed cross-couplings of propargylic halides |
| title_sort | progress in nucleophilic catalysis and development of nickel catalyzed cross couplings of propargylic halides |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/49745 |
| work_keys_str_mv | AT smithseanwseanwesley progressinnucleophiliccatalysisanddevelopmentofnickelcatalyzedcrosscouplingsofpropargylichalides |