Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction

Brett R. Ambler; Ben W.H. Turnbull; Sankar Rao Suravarapu; Maulen M. Uteuliyev; Nancy O. Huynh; Michael J. Krische

doi:10.1021/jacs.8b05724

Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction

Brett R. Ambler
, Ben W.H. Turnbull
, Sankar Rao Suravarapu
, Maulen M. Uteuliyev
, Nancy O. Huynh
, Michael J. Krische

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

Abstract

The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by (R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the "bay region" substructure of the angucycline natural product arenimycin was prepared.

Original language	English (US)
Pages (from-to)	9091-9094
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	140
Issue number	29
DOIs	https://doi.org/10.1021/jacs.8b05724
State	Published - Jul 25 2018
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b05724

Cite this

Ambler, B. R., Turnbull, B. W. H., Suravarapu, S. R., Uteuliyev, M. M., Huynh, N. O., & Krische, M. J. (2018). Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction. Journal of the American Chemical Society, 140(29), 9091-9094. https://doi.org/10.1021/jacs.8b05724

Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction. / Ambler, Brett R.; Turnbull, Ben W.H.; Suravarapu, Sankar Rao et al.
In: Journal of the American Chemical Society, Vol. 140, No. 29, 25.07.2018, p. 9091-9094.

Research output: Contribution to journal › Article › peer-review

Ambler, BR, Turnbull, BWH, Suravarapu, SR, Uteuliyev, MM, Huynh, NO & Krische, MJ 2018, 'Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction', Journal of the American Chemical Society, vol. 140, no. 29, pp. 9091-9094. https://doi.org/10.1021/jacs.8b05724

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abstract = "The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by (R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the {"}bay region{"} substructure of the angucycline natural product arenimycin was prepared.",

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Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction

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