193685-91-5Relevant academic research and scientific papers
Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols
Horino, Yoshikazu,Murakami, Miki,Aimono, Ataru,Lee, Jun Hee,Abe, Hitoshi
supporting information, p. 476 - 480 (2019/01/14)
The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.
Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio- and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through Cyclodimerization of 1-Ethynyl-2-propenyl Esters
Zhao, Jidong,Yang, Shuang,Xie, Xin,Li, Xiangdong,Liu, Yuanhong
, p. 1287 - 1297 (2018/02/09)
Gold(I) complexes bearing sterically demanding phosphine ligands such as tBuXphos catalyze the cascade Rautenstrauch rearrangement/[4 + 3] cycloaddition of 1-ethynyl-2-propenyl esters. The reaction provides an efficient and straightforward rout
Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement
Yang, Lu,Zeng, Qingle
, p. 3149 - 3156 (2017/07/12)
A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.
Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives
Cheng, Cang,Ge, Luo,Lu, Xuehe,Huang, Jianping,Huang, Haocheng,Chen, Jie,Cao, Weiguo,Wu, Xiaoyu
, p. 6866 - 6874 (2016/10/04)
A highly efficient cascade sequence for syntheses of 2,3-disubstituted imidazo[1,2-a]pyridines with exclusive regioselectivity in moderate to excellent yields has been developed. This cascade was initiated through propargylation of 2-aminopyridines at pyridine-nitrogen with propargyl alcohol derivatives using Cu(II)-Pybox as catalyst and followed by an intramolecular cyclization and isomerization. Besides 2-aminopyridine, less reactive 2-aminopyrimidine, 2-aminopyrazine and 3-aminopyridazine were also suitable in this cascade.
Convenient synthesis of allenylphosphoryl compounds: Via Cu-catalysed couplings of P(O)H compounds with propargyl acetates
Shen, Ruwei,Luo, Bing,Yang, Jianlin,Zhang, Lixiong,Han, Li-Biao
supporting information, p. 6451 - 6454 (2016/05/24)
A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.
Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO
Brancour, Celia,Fukuyama, Takahide,Ohta, Yuko,Ryu, Ilhyong,Dhimane, Anne-Lise,Fensterbank, Louis,Malacria, Max
supporting information; experimental part, p. 5470 - 5472 (2010/09/18)
A novel [5+1] type carbonylative cycloaddition reaction has been developed using a Rh complex as catalyst. This reaction can convert readily available 3-acyloxy-1,4-enynes and CO to a wide range of functionalized resorcinols in good yields. A mechanism involving Rh-catalyzed cyclocarbonylation of 3-acyloxy-1,4-enynes accompanied by a 1,2-acyloxy shift is proposed for the present [5+1] type cycloaddition reaction. The Royal Society of Chemistry 2010.
Enantioselective copper-catalyzed propargylic amination
Detz, Remko J.,Delville, Marielle M. E.,Hiemstra, Henk,Van Maarseveen, Jan H.
, p. 3777 - 3780 (2008/12/23)
(Chemical Equation Presented) A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R = Ar) into their amine counterparts in high yield and with good selectivity (up to 88% ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA = diisopropylethylamine).
Organotin Nucleophiles. 5. Palladium-Catalyzed Allylic Propargylation with Allenylstannane
Keinan, Ehud,Peretz, Moshe
, p. 5302 - 5309 (2007/10/02)
Allenyltrialkylstannanes were found to react with various allylic acetates in the presence of catalytic amounts of Pd(PPh3)4 under mild neutral conditions, providing a novel approach for obtaining the 1,5-enyne carbon skeleton.The regioselectivity of propargylation depends largely on the electron-withdrawing properties of the substituents at the two ends of the allylic system: substitution occurs at the end of closer proximity to the more electronegative group.Allylic cyanohydrin acetates are substituted at a position α to the cyano group along with formation of a reduced side product.Several mechanistic aspects of these reactions are discussed.
