Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
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| Format: | Thesis |
| Language: | eng |
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Massachusetts Institute of Technology
2009
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| Online Access: | http://hdl.handle.net/1721.1/46029 |
| _version_ | 1826203724049022976 |
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| author | Son, Sunghee |
| author2 | Gregory C. Fu. |
| author_facet | Gregory C. Fu. Son, Sunghee |
| author_sort | Son, Sunghee |
| collection | MIT |
| description | Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008. |
| first_indexed | 2024-09-23T12:42:03Z |
| format | Thesis |
| id | mit-1721.1/46029 |
| institution | Massachusetts Institute of Technology |
| language | eng |
| last_indexed | 2024-09-23T12:42:03Z |
| publishDate | 2009 |
| publisher | Massachusetts Institute of Technology |
| record_format | dspace |
| spelling | mit-1721.1/460292019-04-12T14:33:32Z Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis Son, Sunghee 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, 2008. Vita. Includes bibliographical references. In Part I, nickel-catalyzed asymmetric carbon-carbon bond-forming reactions are described. A nickel/Pybox system effectively catalyzes regio- and enantioselective cross-couplings between racemic secondary allylic chlorides and readily available alkylzinc halides. This method is applied to generate two stereo centers in a formal total synthesis of fluvirucinine A1. In Part II, the use of planar-chiral compounds as ligands or catalysts in organic synthesis is described. A C2-symmetric planar-chiral bipyridine is an efficient ligand for copper-catalyzed asymmetric [4+1]-cycloadditions between enones and diazoacetates to form 2,3-dihydrofurans. The highly substituted dihydrofurans are not only obtained in good stereoselectivity but also readily converted to other useful molecules. This method is applied to the first catalytic enantioselective synthesis of a deoxy-C-nucleoside. The synthesis of new C2-symmetric planar-chiral catalysts is described. The diastereoslective functionalization of ferrocene using a chiral directing group enables the formation of a number of amines in enantiopure form. These catalysts are tested as several asymmetric catalysts. by Sunghee Son. Ph.D. 2009-06-30T17:05:09Z 2009-06-30T17:05:09Z 2008 2008 Thesis http://hdl.handle.net/1721.1/46029 367593013 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 185 p. application/pdf Massachusetts Institute of Technology |
| spellingShingle | Chemistry. Son, Sunghee Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title | Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title_full | Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title_fullStr | Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title_full_unstemmed | Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title_short | Nickel-catalyzed asymmetric cross-couplings of secondary allylic chlorides and planar-chiral compounds in asymmetric synthesis |
| title_sort | nickel catalyzed asymmetric cross couplings of secondary allylic chlorides and planar chiral compounds in asymmetric synthesis |
| topic | Chemistry. |
| url | http://hdl.handle.net/1721.1/46029 |
| work_keys_str_mv | AT sonsunghee nickelcatalyzedasymmetriccrosscouplingsofsecondaryallylicchloridesandplanarchiralcompoundsinasymmetricsynthesis |