26644-92-8Relevant articles and documents
Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones
Komatsuki, Keiichi,Sadamitsu, Yuta,Sekine, Kohei,Saito, Kodai,Yamada, Tohru
supporting information, p. 11594 - 11598 (2017/09/11)
Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.
Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution
Haug, Timm T.,Harschneck, Tobias,Duschek, Alexander,Lee, Chang-Uk,Binder, J?rg T.,Menz, Helge,Kirsch, Stefan F.
experimental part, p. 510 - 514 (2009/06/05)
Gold-catalyzed reactions of 3-silyloxy-1,4-enynes with alcohols afford primary, secondary, and tertiary pent-2-en-4-ynyl ethers in moderate to excellent yields. The substitution proceeds with high regioselectivity. An initial cyclization providing five-me
A general and facile synthesis of substituted furans by palladium- catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols
Gabriele,Salerno,Lauria
, p. 7687 - 7692 (2007/10/03)
A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 °C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.
Catalytic isomerization of 1-alkynyl-2,3-epoxy alcohols to substituted furans: Succinct routes to furanoid fatty acids and difurylmethanes
Marson, Charles M.,Harper, Steven
, p. 9223 - 9231 (2007/10/03)
A versatile procedure for the preparation of synthetically valuable 2,5- disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)- catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic α- alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(α hydroxyalkyl)furans 4.