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Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives.

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https://www.repository.cam.ac.uk/handle/1810/250533

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Holt & Gaunt 2015 Angewandte Chemie International Edition.pdf (1.02 MB)

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Article

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Abstract

A novel method for the synthesis of a wide range of functionalized 1,3-diol derivatives is reported. Employing a copper-catalyzed oxy-alkenylation strategy, a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts combine to form syn-1,3-carbonates in excellent yield and with high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide-like fragments.

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Keywords

copper, diols, homogeneous catalysis, hypervalent compounds, synthetic methods, Alkenes, Carbonates, Catalysis, Copper, Onium Compounds, Oxygen, Propanols

Journal Title

Angew Chem Int Ed Engl

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Journal ISSN

1433-7851
1521-3773

Volume Title

54

Publisher

Wiley

Publisher DOI

https://doi.org/10.1002/anie.201501995

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Sponsorship
Engineering and Physical Sciences Research Council (EP/I00548X/1)
We are grateful to the EPSRC (D.H.) for a studentship and the ERC and EPSRC for fellowships (M.J.G.).

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Scholarly Works - Chemistry
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