Transformations of 4,5-Substituted (4S,5S)-2,2-Dimethyl-1,3-dioxolanes |
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Authors: | B A Shainyan M V Ustinov L O Nindakova |
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Institution: | (1) Siberian Division, Russian Academy of Sciences, Faworsky Irkutsk Institute of Chemistry, Irkutsk, 664033, Russia |
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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 -acetamidocinnamic and itaconic acids. |
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