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Catalytic Asymmetric Alkylations of Latent Enolates

Nardone, Michael (2016) Catalytic Asymmetric Alkylations of Latent Enolates. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Transition metal-catalyzed asymmetric allylic alkylations have become increasingly important in constructing highly versatile carbon-carbon and carbon-heteroatom bonds. However, diastereoselective allylic alkylations capable of setting vicinal stereocenters remain rare. The text
herein describes a Ru(II)-catalyzed allylic alkylation that utilizes silyl enol ether nucleophiles to provide α,β-substituted-γ,δ-unsaturated acyl pyrroles in synthetically useful diastereoselectivities. To illustrate the value of the resulting products, the methodology was exploited to construct the core of a pharmacologically active target, actinoranone.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Nardone, Michaelmjn22@pitt.eduMJN22
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairNelson, Scott
Committee MemberMeyer, Tara
Committee MemberLiu,
Committee MemberMcDermott, Lee
Date: 8 June 2016
Date Type: Publication
Defense Date: 5 January 2016
Approval Date: 8 June 2016
Submission Date: 26 February 2016
Access Restriction: 1 year -- Restrict access to University of Pittsburgh for a period of 1 year.
Number of Pages: 151
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: Ruthenium(II)-catalysis; Asymmetric Allylic Alkylation, Silyl Enolates, Actinoranone, Pyridyl Imidazoline, Acyl Pyrrole,
Date Deposited: 08 Jun 2016 14:12
Last Modified: 08 Jun 2017 05:15


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