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The Application of Ruthenium(II) and Iridium(I) Complexes to the Synthesis of Complex Organic Products

Liberatore, Richard (2018) The Application of Ruthenium(II) and Iridium(I) Complexes to the Synthesis of Complex Organic Products. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

The application of transition metals to the synthesis complex organic products has become an extremely important facet of chemistry in the last few decades. Such metal complexes exhibit remarkable activity in the construction of new carbon-carbon or carbon-heteroatom bonds in both catalytic and asymmetric fashion. The advance in organometallic chemistry has allowed chemists to access new structural scaffolds while also minimizing the use of stoichiometric reagents. The document herein details the application of iridium(I) and ruthenium(II) complexes to the synthesis of complex organic products. Iridium(I) compounds display good activity in the chemoselective isomerization of di(allyl) ethers and carbonates to access allyl vinyl compounds which are classic substrates for Claisen rearrangements. Ruthenium(II) catalysis can provide α,β-substituted-γ,δ-unsaturated aldehydes and amides from allyl vinyl species such as allyl vinyl ethers, carbonatres, silyl enol ethers and allyl acetates. Our methodology was utilized in the construction of the active core of a potential cancer therapeutic, actinoranone.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Liberatore, Richardrjliberatore@gmail.comrjl48
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scottsgnelson@pitt.edu
Committee MemberHorne, W. Swthhorne@pitt.edu
Committee MemberIslam, Kabirulkai27@pitt.edu
Committee MemberZhang, Linzhanglx@upmc.edu
Date: 28 June 2018
Date Type: Publication
Defense Date: 6 October 2017
Approval Date: 28 June 2018
Submission Date: 3 January 2018
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 236
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: organic synnthesis, ruthenium catalysis, asymmetric catalysis, natural product synthesis
Date Deposited: 28 Jun 2018 15:41
Last Modified: 28 Jun 2018 15:41
URI: http://d-scholarship.pitt.edu/id/eprint/33679

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