Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents | Zendy

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

Open Access

Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents

Author(s) -

Raphael K. Klake,

Samantha L. Gargaro,

Skyler L. Gentry,

Sharon O. Elele,

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.9b02973

Subject(s) - chemistry , stereoselectivity , catalysis , selectivity , combinatorial chemistry , chiral ligand , ligand (biochemistry) , coupling (piping) , enantioselective synthesis , organic chemistry , receptor , mechanical engineering , biochemistry , engineering

We report the development of a stereoselective method for the allylation of ketones utilizing N -substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocontrol. This methodology allows access to chiral γ-hydroxyaldehyde equivalents that were applied in the synthesis of chiral γ-lactones and 2,5-disubstitued tetrahydrofurans.

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