Copper-Catalyzed Oxy-Alkenylation of Homoallylic Alcohols to Generate Functional syn-1,3-Diol Derivatives.
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Authors
Holt, Dean
Gaunt, Matthew J
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.
Description
Keywords
copper, diols, homogeneous catalysis, hypervalent compounds, synthetic methods, Alkenes, Carbonates, Catalysis, Copper, Onium Compounds, Oxygen, Propanols
Journal Title
Angew Chem Int Ed Engl
Conference Name
Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
54
Publisher
Wiley
Publisher DOI
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.).