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.
|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|
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