Stripping off Water at Ambient Temperature: Direct Atom-Efficient Acetal Formation between Aldehydes and Diols Catalyzed by Water-Tolerant and Recoverable Vanadyl Triflate
journal contributionposted on 21.07.2005, 00:00 authored by Chien-Tien Chen, Shiue-Shien Weng, Jun-Qi Kao, Chun-Cheng Lin, Mi-Dan Jan
Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN 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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ambient temperatureCH 3 CNAldehydeAcetalRecoverable Vanadyl Triflate Aromatic aldehydeshydroxyl unitsregioselectiveglucopyranosidevanadyl triflatereductive acetal openingsequentialFormationcombinationdiolfunctionalizationStrippingcatalystchemoselective acylationstitle methodDiols CatalyzedyieldAmbient