7065-27-2Relevant academic research and scientific papers
Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group
Liu, Zhen,Derosa, Joseph,Engle, Keary M.
supporting information, p. 13076 - 13081 (2016/10/13)
A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein selectivity is controlled by a cleavable bidentate directing group. Under the optimized reaction conditions, both dialkyl and alkylaryl alkyne substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.
Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts
Pauli, Larissa,Tannert, Re,Scheil, Robin,Pfaltz, Andreas
supporting information, p. 1482 - 1487 (2015/01/30)
Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.
Efficient synthesis of substituted 3-iodofurans by electrophilic cyclization of propargylic oxirane derivatives
Xie, Yong-Xin,Liu, Xue-Yuan,Wu, Lu-Yong,Han, Yao,Zhao, Lian-Biao,Fan, Ming-Jin,Liang, Yong-Min
experimental part, p. 1013 - 1018 (2009/04/11)
The electrophilic cyclization of various propargylic oxirane compounds and I2 offers an efficient and straightforward route to highly substituted iodofurans under mild reaction conditions. Further functionalization has demonstrated that the iod
Regioselective ring opening of α-substituted α-alkynyl oxiranes to 2-substituted 3-butyn-1-ols
Nussbaumer, Peter,Stuetz, Anton
, p. 7507 - 7508 (2007/10/02)
Treatment of α-substituted α-acetylenic epoxides with DIBAH in THF provides 2-substituted 3-butyn-1-ols in high yield avoiding propargyl/allene isomerization.
Reactivity and Reactions of Aromatic Acetylenic Acids and Ketones
Drewes, Siegfried E.,Douglass, Deborah,Malissar, Dean G. S.,Roos, Gregory H. P.,Kaye, Perry T.
, p. 1507 - 1511 (2007/10/02)
Some novel reactions of the acetylenic carboxylic acid, 4-oxo-6-phenylhexynoic acid with succinic anhydride are described.One of the products of the reaction is a butyrolactone derivative.Transformation of 4-phenylbut-3-yn-2-one results in the formation of α,β-acetylenic-α'-alkoxy epoxides which are of interest as anti-tumor compounds.
A new furan annelation reaction by the palladium-catalyzed reaction of 2-alkynyl carbonates or 2-(1-alkynyl)oxiranes with β-keto esters
Minami, Ichiro,Yuhara, Masami,Watanabe, Hiroyuki,Tsuji, Jiro
, p. 225 - 242 (2007/10/02)
A new furan annelation by the palladium-catalyzed reaction of 2-alkynyl carbonates with β-keto esters is described.The reaction proceeds under mild neutral conditions and hence unstable 3-alkylidene-2,3-dihydrofurans can be prepared in this way.Similarly,
