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  • Title: Stripping off water at ambient temperature: direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate.
    Author: Chen CT, Weng SS, Kao JQ, Lin CC, Jan MD.
    Journal: Org Lett; 2005 Jul 21; 7(15):3343-6. PubMed ID: 16018656.
    Abstract:
    [reaction: see text]. Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH(3)CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.
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