Silylcupration of Conjugated Alkynes and Copper-Hydride Reductions of Morita-Baylis-Hillman Adducts
- Degree Grantor:
- University of California, Santa Barbara. Chemistry
- Degree Supervisor:
- Bruce H. Lipshutz
- Place of Publication:
- [Santa Barbara, Calif.]
- Publisher:
- University of California, Santa Barbara
- Creation Date:
- 2015
- Issued Date:
- 2015
- Topics:
- Organic chemistry
- Genres:
- Online resources and Dissertations, Academic
- Dissertation:
- M.S.--University of California, Santa Barbara, 2015
- Description:
There currently exists a need for more extensive mild and greener bond forming reactions that allow for construction of sophisticated carbon frameworks. Vinylsilanes have proven themselves to be valuable intermediates in organic synthesis. Traditionally, these educts have been difficult to access requiring stoichiometric metals which often precudes their use on scale. Herein, we investigated the use of Suginome's reagent, PhMe2SiBpin, in a commercially available surfactant TPGS-750-M to afford isomerically pure (E)-beta-silyl-substituted carbonyl derivatives by way of a copper catalyzed silylcupration in water at room temperature.
Copper hydride has seen extensive use as both an asymmetric and achiral source of hydride for many decades. We were interested in investigating copper hydride's application toward Morita-Baylis-Hillman adducts given their possession of multiple electrophilic sites. We discovered that CuH could be used for tandem reductions of racemic MBH ketones lacking defined olefin geometry into valuable chiral allylic alcohol derivatives with defined stereochemistry.
- Physical Description:
- 1 online resource (101 pages)
- Format:
- Text
- Collection(s):
- UCSB electronic theses and dissertations
- Other Versions:
- http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqm&rft_dat=xri:pqdiss:10011329
- ARK:
- ark:/48907/f3w958qk
- ISBN:
- 9781339471600
- Catalog System Number:
- 990046180050203776
- Copyright:
- Carl Peterson, 2015
- Rights:
In Copyright
- Copyright Holder:
- Carl Peterson
File | Description |
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Access: Public access | |
Peterson_ucsb_0035N_12751.pdf | pdf (Portable Document Format) |