Synfacts 2018; 14(10): 1043
DOI: 10.1055/s-0037-1610889
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Intermolecular Ruthenium-Catalyzed Cycloaddition

Hisashi Yamamoto
Wataru Muramatsu
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
Further Information

Publication History

Publication Date:
17 September 2018 (online)



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.



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.