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Development of E-and Z-Selective Base-Catalyzed Redox Isomerizations and Ene-Diene Cross Metathesis

Sonye, John P. (2006) Development of E-and Z-Selective Base-Catalyzed Redox Isomerizations and Ene-Diene Cross Metathesis. Master's Thesis, University of Pittsburgh. (Unpublished)

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γ-Oxo-α,β-alkenoates are found in several natural products and are versatile syntheticintermediates. We have developed methods to selectively prepare E and Z-alkenoates from γ-hydroxy-α,β-alkynoates wherein the optimization, mechanism, and scope of the reactions are described. Biological testing of γ-oxo-α,β-alkenoates and their derivatives in zebrafish embryos also are discussed.Since the development of ruthenium alkylidene catalysts, olefin metathesis has become auseful method in synthetic organic chemistry. However, certain areas of metathesis haveremained under-researched; in particular, the cross metathesis of a 1,3-diene with a terminalolefin known as ene-diene cross metathesis (EDCM). The attempt at optimization of EDCMreactions using a general model is also discussed.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Sonye, John P.jps26@pitt.eduJPS26
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairKoide, Kazunorikoide@pitt.eduKOIDE
Committee MemberSchafmeister, Christian Emeister@pitt.eduMEISTER
Committee MemberFloreancig, Paul Eflorean@pitt.eduFLOREAN
Date: 29 June 2006
Date Type: Completion
Defense Date: 27 April 2006
Approval Date: 29 June 2006
Submission Date: 22 April 2006
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: cross metathesis; diene; redox isomerization; zebrafish
Other ID:, etd-04222006-201629
Date Deposited: 10 Nov 2011 19:40
Last Modified: 15 Nov 2016 13:41


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