Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8574120

Reference Type

Journal Article

Title

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

Author(s)

Ambler, BR; Turnbull, BWH; Suravarapu, SR; Uteuliyev, MM; Huynh, NO; Krische, MJ

Year

2018

Is Peer Reviewed?

Yes

Journal

Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126

Publisher

American Chemical Society

Volume

140

Issue

Page Numbers

9091-9094

Language

English

DOI

10.1021/jacs.8b05724

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. Â© 2018 American Chemical Society.