131292-14-3Relevant articles and documents
Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction
Liang, Ren-Xiao,Song, Ling-Jie,Lu, Jin-Bo,Xu, Wei-Yan,Ding, Chao,Jia, Yi-Xia
supporting information, p. 7412 - 7417 (2021/03/01)
The extensively developed ene-type enantioselective cycloisomerization of classical 1,n-enynes provides an efficient approach to chiral cyclic 1,4-dienes. In contrast, the catalytic asymmetric heteroarenyne (heteroarene–alkyne) cycloisomerization involving the dearomative transformation of endocyclic aromatic C=C bonds remains unknown. Herein, we communicate a PdH-catalyzed enantioselective heteroarenyne cycloisomerization reaction of alkyne-tethered indole substrates (formal 1,5- and 1,6-enynes). Based on this strategy, a variety of structurally diverse chiral spiro and fused indoline derivatives bearing quaternary stereocenters and exocyclic C=C bonds are afforded in moderate to excellent yields and excellent enantioselectivities (up to 98 % ee). The classical ene-type enantioselective 1,5-enyne cycloisomerization of N-vinylpropiolamides is also developed to afford chiral 2-pyrrolones in good to excellent ee values.
Gold-catalyzed cyclization and subsequent arylidene group transfer of O-propioloyl oximes
Nakamura, Itaru,Okamoto, Masashi,Terada, Masahiro
supporting information; experimental part, p. 2453 - 2455 (2010/07/05)
Gold-catalyzed cyclizations of O-propioloyl oximes via C-N bond formation followed by arylidene group transfer were successfully carried out to afford the corresponding 4-arylideneisoxazol-5(4H)-ones in good to excellent yields. As an example, (E)-benzaldehyde O-3-phenylpropioloyl oxime (1a) was reacted in acetonitrile at 25 °C in the presence of Au(PPh3)NTf2 (5 mol %) to give 4-benzylidene-3-phenylisoxazol-5(4H)-one (2a) in 90% yield. On the basis of crossover experiments, the arylidene "migration" was shown to proceed in an intermolecular manner.
Synthesis-driven mapping of the dictyodendrin alkaloids
Buchgraber, Philipp,Domostoj, Mathias M.,Scheiper, Bodo,Wirtz, Conny,Mynott, Richard,Rust, J?rg,Fürstner, Alois
experimental part, p. 6519 - 6534 (2011/02/26)
The dictyodendrin alkaloids have been described as the first telomerase inhibitors of marine origin. As such they represent interesting lead compounds in the quest for small molecule inhibitors of this tumor-marker enzyme. Described herein is the preparat