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Transformations of 4,5-Substituted (4S,5S)-2,2-Dimethyl-1,3-dioxolanes

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Abstract

(4S,5S)-4,5-Bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane treated with trifluoromethanesulfonyl chloride in pyridine undergoes tandem substitution of one hydroxy group by a triflate group, and the other by pyridinium moiety. In neutral solvents the (4S,5S)-4,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane dilithium salt reacts with trifluoromethanesulfonyl chloride affording both triflates and chlorides and also suffers a cleavage of the dioxolane ring followed by transformations of acyclic products. A triflate cationic complex rhodium cyclooctadiene (4S,5S)-2,3-dihydroxy-1,4-bis(dimethylamino)-2,3-O-isopropylidenebutane was prepared and used as catalyst for hydrogenation of α-acetamidocinnamic and itaconic acids.

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Authors and Affiliations

  1. Siberian Division, Russian Academy of Sciences, Faworsky Irkutsk Institute of Chemistry, Irkutsk, 664033, Russia

    B. A. Shainyan, M. V. Ustinov & L. O. Nindakova

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  1. B. A. Shainyan
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  2. M. V. Ustinov
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  3. L. O. Nindakova
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Shainyan, B.A., Ustinov, M.V. & Nindakova, L.O. Transformations of 4,5-Substituted (4S,5S)-2,2-Dimethyl-1,3-dioxolanes. Russian Journal of Organic Chemistry 37, 1757–1761 (2001). https://doi.org/10.1023/A:1013986304683

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