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DOI: 10.1055/s-0043-1763924
Cobalt-Mediated Intramolecular Cyclization of Bis-homoallylic Alcohols under Aerobic Conditions
A Convenient Method for the Stereoselective Preparation of trans-2-Hydroxymethyltetrahydrofurans by the Oxidative Cyclization of 5-Hydroxy-1-alkenes with Molecular Oxygen Catalyzed by Cobalt(II) Complex.
Chem. Lett. 1990;
19: 67-70
Significance
Inoki and Mukaiyama report an intramolecular dioxygenation of bis-homoallylic alcohols to achieve a highly diastereoselective synthesis of trans-substituted tetrahydrofurans. These oxygenated motifs are found in a wide range of natural products. This methodology and developments have been applied to many synthetic efforts towards complex natural products.
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Comment
Under non-optimized conditions Mukaiyama reported that hydroalkoxylation, rather than dioxygenation of the pendant alkene was observed as a significant byproduct via the reduction of III. Access to these reduced products and other highly functionalized tetrahydrofurans has been developed by Hartung and co-workers (see: J. Am. Chem. Soc. 2009, 131, 12918; J. Am. Chem. Soc. 2011, 133, 3906) using other radical acceptors.
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Publikationsverlauf
Artikel online veröffentlicht:
15. April 2024
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