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 | Zendy

Samantha L. Gargaro | Zendy; Raphael K. Klake | Zendy; Kevin L. Burns | Zendy; Sharon O. Elele | Zendy; Skyler L. Gentry | Zendy; Joshua D. Sieber | Zendy

Open Access

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

Author(s) -

Samantha L. Gargaro,

Raphael K. Klake,

Kevin L. Burns,

Sharon O. Elele,

Skyler L. Gentry,

Joshua D. Sieber

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03937

Subject(s) - umpolung , chemistry , synthon , vicinal , catalysis , stereoselectivity , reagent , selectivity , nucleophile , combinatorial chemistry , organic chemistry , stereochemistry

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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