Gold(I)-catalysed alcohol additions to cyclopropenes.
نویسندگان
چکیده
Gold(i)-catalysed addition of alcohols to 3,3-disubstituted cyclopropenes occurs in a highly regioselective and facile manner to produce alkyl tert-allylic ethers in good yields. The reaction is tolerant of sterically hindered substituents on the cyclopropene as well as primary and secondary alcohols as nucleophiles. In this full article, we report on the substrate scope and plausible mechanism, as well as the regioselectivity issues arising from subsequent gold(i)-catalysed isomerisation of tertiary to primary allylic ethers.
منابع مشابه
Gold catalysed reactions with cyclopropenes.
Gold(i) catalyses the ring-opening addition of cyclopropenes in a mild and regioselective manner.
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Gold(I)-catalysed reaction between cyclopropenes and furans produces functionalised conjugated trienes. The reaction is mild, facile and proceeds with very low catalyst loadings.
متن کاملComputational studies on the mechanism of the gold(I)-catalysed rearrangement of cyclopropenes.
Density functional theory calculations have been employed to investigate the mechanism of gold(I)-catalysed rearrangements of cyclopropenes. Product formation is controlled by the initial ring-opening step which results in the formation of a gold-stabilised carbocation/gold carbene intermediate. With 3-phenylcyclopropene-3-methylcarboxylate, the preferred intermediate allows cyclisation via nuc...
متن کاملTheoretical study on the ring-opening reactions of cyclopropenes mediated by a AuI complex.
DFT calculations have been carried out in order to rationalize and predict the ring-opening regioselectivity of substituted cyclopropenes in the presence of gold(I) catalysts. It has been shown that the regioselectivity of these ring-opening processes is driven by the relative π-donor ability of the substituents on the cyclopropene double bond (C1 and C2). A stronger π-donor substituent at C2 f...
متن کاملWhen cyclopropenes meet gold catalysts
Cyclopropenes as substrates entered the field of gold catalysis in 2008 and have proven to be valuable partners in a variety of gold-catalyzed reactions. The different contributions in this growing research area are summarized in this review.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 18 شماره
صفحات -
تاریخ انتشار 2010