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Synfacts 2018; 14(10): 1043
DOI: 10.1055/s-0037-1610889
DOI: 10.1055/s-0037-1610889
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Intermolecular Ruthenium-Catalyzed Cycloaddition
Ambler BE.
Turnbull BW. H.
Suravarapu SR.
Uteuliyev MM.
Huynh NO.
Krische MJ.
* University of Texas at Austin, USA
Enantioselective Ruthenium-Catalyzed Benzocyclobutenone–Ketol Cycloaddition: Merging C–C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.
J. Am. Chem. Soc. 2018;
140: 9091-9094
Enantioselective Ruthenium-Catalyzed Benzocyclobutenone–Ketol Cycloaddition: Merging C–C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.
J. Am. Chem. Soc. 2018;
140: 9091-9094
Further Information
Publication History
Publication Date:
17 September 2018 (online)
Key words
ruthenium catalysis - cycloaddition - C–C activation - transfer hydrogenation - polyketides
Significance
Metal-catalyzed cycloaddition is one of the most active areas of research. The authors have developed an enantioselective intermolecular cycloaddition of benzocyclobutenones with tetralone-derived ketols through a C–C bond oxidative addition catalyzed by a chiral ruthenium–DM-SEGPHOS complex.
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Comment
This ruthenium-catalyzed intermolecular cycloaddition merging C–C bond activation and transfer hydrogenative coupling proceeds smoothly in moderate to high yield with excellent enantio-, diastereo-, and regioselectivities. The obtained products can be transformed into the corresponding compounds containing dione and amine motifs.
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