2 options
N-heterocyclic carbenes: From design to synthesis and their application as nucleophilic catalysts.
- Format:
- Book
- Thesis/Dissertation
- Author/Creator:
- Struble, Justin R.
- Language:
- English
- Subjects (All):
- Chemistry, Organic.
- 0490.
- Penn dissertations--Chemistry.
- Chemistry--Penn dissertations.
- Local Subjects:
- Penn dissertations--Chemistry.
- Chemistry--Penn dissertations.
- 0490.
- Physical Description:
- 428 pages
- Contained In:
- Dissertation Abstracts International 71-04B.
- System Details:
- Mode of access: World Wide Web.
- text file
- Summary:
- Our group has pioneered novel internal redox process of aldehydes possessing an internal alpha-reducible functionality mediated by N-heterocyclic carbenes (NHCs). Two discrete discoveries have been crucial to the success of our program. The first has been the identification of reaction parameters intimately related to the fate of the putative reactive intermediates to exquisitely allow access to a single reaction outcome (e.g. NHC-enolate vs homoenolate). The second, and more crucial, has been the development of new N-mesityl substituted triazolium and imidazolium salts that serve as precursors to the N-heterocyclic carbene nucleophilic catalyst. Our achiral and chiral, bicyclic N-mesityl triazolium salts have shown unprecedented reactivity and selectivity in a variety of conceptually new transformations. As such we have been the first to disclose highly enantioselective intermolecular annulations providing access to stereochemically rich heterocycles. Moreover, the synthesis of a novel N-mesityl aminoindanol-derived imidazolium salt allowed for the first time the investigation into the inherent reactivity differences that exist between two classes of NHCs (triazolium vs. imidazolium). Current efforts toward catalyst development via a combinatorial approach promise the opportunity to discover new enantioselective NHC-catalyzed processes.
- Notes:
- Thesis (Ph.D. in Chemistry) -- University of Pennsylvania, 2009.
- Source: Dissertation Abstracts International, Volume: 71-04, Section: B, page: 2410.
- Adviser: Jeffrey Bode.
- Local Notes:
- School code: 0175.
- ISBN:
- 9781109710496
- Access Restriction:
- Restricted for use by site license.
The Penn Libraries is committed to describing library materials using current, accurate, and responsible language. If you discover outdated or inaccurate language, please fill out this feedback form to report it and suggest alternative language.