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Issue 19, 2008
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Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols

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Abstract

Bishomoallylic alcohols (pent-4-en-1-ols) underwent efficient oxidative cyclizations, if treated with O2 and bis{2,2,2-trifluoromethyl-1-[(1R,4S)-1,7,7-trimethyl-2-(oxo-κO)bicyclo[2.2.1]hept-3-yliden]ethanolato-κO}cobalt(II) in solutions of 2-propanol at 60 °C. Ring closures occurred diastereoselectively and afforded 2,3-trans- (96% de), 2,4-cis- (∼60% de), and 2,5-trans-substituted (>99% de) (phenyl)tetrahydrofur-2-ylmethanols as major components. Formation of bicyclic compounds and a 2,3,4,5-substituted oxolane was feasible as exemplified by syntheses of oxabicyclo[4.3.0]nonylmethanols and a derivative of natural product magnosalicin in 61–72% (90–99% de). The effectiveness of tetrahydrofuran synthesis was critically dependent on (i) solvent, (ii) reaction temperature, (iii) initial cobalt concentration, (iv) chain length between hydroxyl and vinyl groups, and (v) substitution at reacting entities. A sequence is proposed for rationalizing observed selectivities.

Graphical abstract: Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols

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Supplementary files

Article information


Submitted
17 Mar 2008
Accepted
05 Jun 2008
First published
16 Jul 2008

Org. Biomol. Chem., 2008,6, 3532-3541
Article type
Paper

Activation of molecular oxygen and its use in stereoselective tetrahydrofuran-syntheses from δ,ε-unsaturated alcohols

B. Menéndez Pérez, D. Schuch and J. Hartung, Org. Biomol. Chem., 2008, 6, 3532
DOI: 10.1039/B804588G

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