Development of a Modified System to Provide Improved Diastereocontrol in the Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenamides

Dang Ho; Samantha Gargaro; Raphael Klake; Joshua Sieber

doi:10.26434/chemrxiv-2021-g2xbm

Working Paper

Abstract

Chiral g-lactones are prevalent organic architectures found in a large array of natural products. In this work, we disclose the development of a modified catalytic system utilizing a commercially available Cu-phosphite catalyst for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral -lactone precursors in 80:20 to 99:1 dr.

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Supplementary material

Characterization data

Spectral data are provided for new compounds.

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Development of a Modified System to Provide Improved Diastereocontrol in the Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenamides

Dang Binh Ho, Samantha Gargaro, Raphael K. Klake, Joshua D. Sieber journal article

The Journal of Organic Chemistry , Volume 87, Issue 4

Online publication date: Nov 22, 2021

Version History

Oct 19, 2021 Version 1

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The content is available under CC BY NC ND 4.0 License CreativeCommons.org

DOI

10.26434/chemrxiv-2021-g2xbm

Funding

Bill and Melinda Gates Foundation

1176590

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

Keywords

catalysis

reductive coupling

allenamides

Publication

This content is an early or alternative research output and has not been peer-reviewed at the time of posting.