Access to a Catalytically Generated Umpolung Reagent through the Use of Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons

We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By employing N-heterocyclic carbenes as ligands for the Cu catalyst, good branched selectivity can be obtained with high diastereocontrol....

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 23; pp. 9753 - 9758
Main Authors Gargaro, Samantha L, Klake, Raphael K, Burns, Kevin L, Elele, Sharon O, Gentry, Skyler L, Sieber, Joshua D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
ALCOHOLS
LIGANDS
NATURAL-PRODUCTS
ALLYLATION
CHEMISTRY
NHC
STEREOSELECTIVE-SYNTHESIS
ELECTROPHILES
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Summary:We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By employing N-heterocyclic carbenes as ligands for the Cu catalyst, good branched selectivity can be obtained with high diastereocontrol. This methodology allows access to a catalytically generated, polarity-reversed (umpolung) allyl nucleophile to enable the preparation of chiral 1,2-aminoalcohol synthons containing a dissonant functional group relationship.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03937