10229-10-4Relevant articles and documents
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Schulte,Goes
, p. 118,124 (1957)
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Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles
Tsukamoto, Hirokazu,Ito, Kazuya,Doi, Takayuki
, p. 5102 - 5105 (2018)
Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.
First total synthesis of (+/-)-taxifolial a and (+/-)-iso-caulerpenyne.
Commeiras,Santelli,Parrain
, p. 1713 - 1715 (2001)
The first synthesis of (+/-)-taxifolial A and iso-caulerpenyne was accomplished. The key steps in the sequence are (1) the stereoselective assembly of a vinyltin derived from butynediol and a functionalized aldehyde and (2) the construction of the dienyne moiety via a Stille cross-coupling.
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Ansell,Brown
, p. 1788,1793 (1957)
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Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes
Liu, Mingyu,Tang, Tianhua,Apolinar, Omar,Matsuura, Rei,Busacca, Carl A.,Qu, Bo,Fandrick, Daniel R.,Zatolochnaya, Olga V.,Senanayake, Chris H.,Song, Jinhua J.,Engle, Keary M.
supporting information, p. 3881 - 3888 (2021/04/06)
Selective carbon-carbon (C-C) bond formation in chemical synthesis generally requires prefunctionalized building blocks. However, the requisite prefunctionalization steps undermine the overall efficiency of synthetic sequences that rely on such reactions, which is particularly problematic in large-scale applications, such as in the commercial production of pharmaceuticals. Herein, we describe a selective and catalytic method for synthesizing 1,3-enynes without prefunctionalized building blocks. In this transformation several classes of unactivated internal acceptor alkynes can be coupled with terminal donor alkynes to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcohols, (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. This method is facilitated by a tailored P,N-ligand that enables regioselective addition and suppresses secondary E/Z-isomerization of the product. The reaction is scalable and can operate effectively with as low as 0.5 mol % catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. We also present preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle.
A copper-catalyzed pyrrolidine and preparation of quinoline derivatives method and application (by machine translation)
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Paragraph 0037; 0039, (2017/08/28)
The invention discloses a pyrrolidine and for preparation of quinoline derivatives, comprises the following steps: the cuprous chloride and aminoalkynes, alkynes are added to a reaction flask, adding the solvent DMF, under microwave irradiation, 150 °C reaction 30 minutes to obtain the target product. The method has high yield, time fast, low cost, for the end of the substrate is not limited to the alkyne, to non-terminalthe alkyne is eventerminal alkyne and has good serviceability, solves the defect of the gold catalytic of this reaction, the method for preparing the compound portion of through the cell active test, with tumor cell proliferation inhibitory activity, indicates this method is in the anti-tumor drug discovery has potential application value. (by machine translation)
