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Asymmetric Copper Catalyzed Addition to Activated Alkenes

Title: Asymmetric Copper Catalyzed Addition to Activated Alkenes.
Name(s): Lackey, Hershel, author
McQuade, Tyler D., professor directing thesis
Dudley, Greg B., committee member
Shatruk, Michael, committee member
Zhu, Lei, committee member
Department of Chemistry and Biochemistry, degree granting department
Florida State University, degree granting institution
Type of Resource: text
Genre: Text
Issuance: monographic
Date Issued: 2011
Publisher: Florida State University
Place of Publication: Tallahassee, Florida
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: This thesis presents the synthesis of a chiral 6-membered NHC catalyst copper catalyst and its use in the β-borylation and allylic substitution reactions. The application of the catalyst in the known β-borylation reaction demonstrates that the catalyst can provide high yields, enatioselectivities, and activity comparable if not improved to traditional 5-membered NHCs and phosphine copper complexes. The 6-membered NHC copper complex was then used in a nucleophilic diboron addition to allylic aryl ethers where the catalyst demonstrated different chemoselectivity compared to 5-membered NHC and phosphine catalyst. Further investigation of this phenomenon led to development of a stereoconvergent, asymmetric reaction which could convert mixtures of E and Z isomers into a single enantiomer in high yield.
Identifier: FSU_migr_etd-3325 (IID)
Submitted Note: A Thesis submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Master of Science.
Degree Awarded: Spring Semester, 2011.
Date of Defense: December 3, 2010.
Keywords: Asymmetric Catalysis, Borylation, Copper, NHC, Organoboronates
Bibliography Note: Includes bibliographical references.
Advisory Committee: Tyler D. McQuade, Professor Directing Thesis; Greg B. Dudley, Committee Member; Michael Shatruk, Committee Member; Lei Zhu, Committee Member.
Subject(s): Chemistry
Persistent Link to This Record:
Owner Institution: FSU

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Lackey, H. (2011). Asymmetric Copper Catalyzed Addition to Activated Alkenes. Retrieved from