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Catalytically Generated Umpolung Reagent
through the Use of Cu-Catalyzed Reductive Coupling of Ketones and
Allenes for the Synthesis of Chiral Vicinal Aminoalcohol Synthons

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Abstract

We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By employing N-heterocyclic carbenes as ligands for the Cu catalyst, good branched selectivity can be obtained with high diastereocontrol. This methodology allows access to a catalytically generated, polarity-reversed (umpolung) allyl nucleophile to enable the preparation of chiral 1,2-aminoalcohol synthons containing a dissonant functional group relationship.

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Most cited references 19

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Is Open Access

Natural products as reservoirs of novel therapeutic agents

Sadaf Mushtaq, Bilal Haider Abbasi, Bushra Uzair … (2018)

Since ancient times, natural products from plants, animals, microbial and marine sources have been exploited for treatment of several diseases. The knowledge of our ancestors is the base of modern drug discovery process. However, due to the presence of extensive biodiversity in natural sources, the percentage of secondary metabolites screened for bioactivity is low. This review aims to provide a brief overview of historically significant natural therapeutic agents along with some current potential drug candidates. It will also provide an insight into pros and cons of natural product discovery and how development of recent approaches has answered the challenges associated with it.

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Author and article information

Journal

Journal ID (nlm-ta): Org Lett

Journal ID (iso-abbrev): Org. Lett

Journal ID (publisher-id): ol

Journal ID (coden): orlef7

Title: Organic Letters

Publisher: American Chemical Society

ISSN (Print): 1523-7060

ISSN (Electronic): 1523-7052

Publication date (Electronic): 26 November 2019

Publication date (Print): 06 December 2019

Volume: 21

Issue: 23

Pages: 9753-9758

Affiliations

[1]Department of Chemistry, Virginia Commonwealth University , 1001 West Main Street, Richmond, Virginia 23284-3028, United States

Author notes

[* ]E-mail: jdsieber@ 123456vcu.edu .

Article

DOI: 10.1021/acs.orglett.9b03937

PMC ID: 6902281

PubMed ID: 31769994

SO-VID: af55059a-8109-46f7-8cdc-744df85ea740

License:

This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.