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  Asymmetric Catalysis with CO2 : The Direct α-Allylation of Ketones

Pupo, G., Properzi, R., & List, B. (2016). Asymmetric Catalysis with CO2: The Direct α-Allylation of Ketones. Angewandte Chemie International Edition, 55(20), 6099-6102. doi:10.1002/anie.201601545.

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 Creators:
Pupo, Gabriele1, Author              
Properzi, Roberta1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: allylic alcohol; atom economy; enol catalysis; quaterary stereocenters; α-allylation
 Abstract: Quaternary stereocenters are found in numerous bioactive molecules. The Tsuji-Trost reaction has proven to be a powerful C-C bond forming process, and, at least in principle, should be well suited to access quaternary stereocenters via the α-allylation of ketones. However, while indirect approaches are known, the direct, catalytic asymmetric α-allylation of branched ketones has been elusive until today. By combining "enol catalysis" with the use of CO2 as a formal catalyst for asymmetric catalysis, we have now developed a solution to this problem: we report a direct, highly enantioselective and highly atom-economic Tsuji-Trost allylation of branched ketones with allylic alcohol. Our reaction delivers products bearing quaternary stereocenters with high enantioselectivity and water as the sole by-product. We expect our methodology to be of utility in asymmetric catalysis and inspire the design of other highly atom-economic transformations.

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Language(s): eng - English
 Dates: 2016-02-122016-04-132016-05-10
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201601545
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 55 (20) Sequence Number: - Start / End Page: 6099 - 6102 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851