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  • Title: The effect of sulfoxides on the stereoselective construction of tetrahydrofurans: total synthesis of (+)-goniothalesdiol.
    Author: Hernández-Torres G, Carreño MC, Urbano A, Colobert F.
    Journal: Chemistry; 2011 Jan 24; 17(4):1283-93. PubMed ID: 21243696.
    Abstract:
    Good to excellent stereoselectivities were achieved in the reductive cyclization (with Et(3)SiH/trimethylsilyl trifluoromethanesulfonate (TMSOTf)) of enantiopure hydroxy sulfinyl ketones en route to 2,5-cis-disubstituted tetrahydrofuran skeletons. Electrostatic effects of the exocyclic sulfoxide, which stabilized the reactive intermediate oxocarbenium conformations, were responsible for the observed stereocontrol. A model is proposed to explain the results. The use of this reaction and the asymmetric β-ketosulfoxide reduction as key steps facilitated the total enantioselective synthesis of the natural β-C-aryl glycoside (+)-goniothalesdiol.
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