Dissertation/Thesis Abstract

Catalytic Asymmetric Alkylations of Latent Enolates
by Nardone, Michael J., Ph.D., University of Pittsburgh, 2016, 152; 10289922
Abstract (Summary)

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.

Indexing (document details)
Advisor: Nelson, Scott G.
School: University of Pittsburgh
School Location: United States -- Pennsylvania
Source: DAI-B 78/03(E), Dissertation Abstracts International
Subjects: Chemistry, Organic chemistry
Keywords: ACVL pyrroles, Allylic alkylation, Asymmetrical catalyst, Ruthenium, Vicinal stereocenters
Publication Number: 10289922
ISBN: 978-1-369-32178-4
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