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Issue 14, 2018
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Stereoselective allylic reduction via one-pot palladium-catalyzed allylic sulfonation and sulfinyl retro-ene reactions

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Abstract

A tandem approach for the stereoselective allylic reduction has been developed based on a strategy combining the palladium-catalyzed S-allylation and the sulfinyl retro-ene reactions. In a one-pot process employing various allylic carbonates, sodium t-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na), easily prepared from the commercially available reagent Rongalite™, serves as a potent nucleophile to engage in the Tsuji–Trost S-allylation reaction generating allylic sulfone products. Subsequently, in situ deprotection of the TBSOMS group reveals allylic sulfinic acids which undergo stereospecific reductive transposition via sulfur dioxide extrusion to provide alkene products.

Graphical abstract: Stereoselective allylic reduction via one-pot palladium-catalyzed allylic sulfonation and sulfinyl retro-ene reactions

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Publication details

The article was received on 05 Mar 2018, accepted on 31 May 2018 and first published on 31 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00233A
Citation: Org. Chem. Front., 2018,5, 2158-2162
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    Stereoselective allylic reduction via one-pot palladium-catalyzed allylic sulfonation and sulfinyl retro-ene reactions

    H. Um, J. Min, T. An, J. Choi and C. Lee, Org. Chem. Front., 2018, 5, 2158
    DOI: 10.1039/C8QO00233A

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