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

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 i...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-06, Vol.54 (27), p.7857-7861
Main Authors: Holt, Dean, Gaunt, Matthew J.
Format: Article
Language:English
Subjects:
Alcohols
Alkenes - chemistry
Carbonates - chemistry
Catalysis
copper
Copper - chemistry
Derivatives
diols
Fragments
homogeneous catalysis
hypervalent compounds
Onium Compounds - chemistry
Oxygen - chemistry
Polyols
Propanols - chemistry
Selectivity
Strategy
Synthesis
synthetic methods
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Summary: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. Polyols: The reported copper‐catalyzed oxy‐alkenylation strategy works well for a range of readily available, substituted homoallylic alcohol derivatives and alkenyl(aryl) iodonium salts to form syn‐1,3‐carbonates in excellent yield and high selectivity. Furthermore, the products formed are amenable to an iterative reaction sequence, thus affording highly complex polyketide‐like fragments.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201501995