286376-22-5Relevant academic research and scientific papers
Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene–Ene–Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism
Cassú, Daniel,Parella, Teodor,Solà, Miquel,Pla-Quintana, Anna,Roglans, Anna
supporting information, p. 14889 - 14899 (2017/10/27)
Allene-(E)-ene-yne N-tosyl-tethered substrates 3 a–3 h were efficiently prepared and their rhodium-catalyzed [2+2+2] cycloaddition reactions were evaluated. The cycloadditions are chemoselective as only the proximal double bond of the allene reacted to af
Preference of Ruthenium-Based Metathesis Catalysts toward Z- and E-Alkenes as a Guide for Selective Reactions to Alkene Stereoisomers
Lee, Jihong,Kim, Kyung Hwan,Lee, Ok Suk,Choi, Tae-Lim,Lee, Hee-Seung,Ihee, Hyotcherl,Sohn, Jeong-Hun
, p. 7591 - 7596 (2016/09/09)
As a guide for selective reactions toward either Z- or E-alkene in a metathesis reaction, the relative preference of metathesis Ru catalysts for each stereoisomer was determined by a method using time-dependent fluorescence quenching. We found that Ru-1 p
Secondary phosphine oxide-gold(I) complexes and their first application in catalysis
Schroeder, Felix,Tugny, Coralie,Salanouve, Elise,Clavier, Herve,Giordano, Laurent,Moraleda, Delphine,Gimbert, Yves,Mouries-Mansuy, Virginie,Goddard, Jean-Philippe,Fensterbank, Louis
supporting information, p. 4051 - 4056 (2014/10/15)
A series of new secondary phosphine oxide (SPO)-gold(I) complexes have been synthesized and characterized by X-ray crystallography. Complexes exhibited dimeric structures interconnected by O-H···Cl hydrogen bonds. Their first use in homogeneous catalysis
Enantioselective IrI-catalyzed carbocyclization of 1,6-enynes by the chiral counterion strategy
Barbazanges, Marion,Auge, Mylene,Moussa, Jamal,Amouri, Hani,Aubert, Corinne,Desmarets, Christophe,Fensterbank, Louis,Gandon, Vincent,Malacria, Max,Ollivier, Cyril
experimental part, p. 13789 - 13794 (2012/01/06)
Enantioenriched bicyclo[4.1.0]hept-2-enes were synthesized by Ir I-catalyzed carbocyclization of 1,6-enynes. No chiral ligands were used, CO and PPh3 were the only ligands bound to iridium. Instead, the stereochemical information was
Rhodium-catalyzed synthesis of γ-butyrolactams and pyrrolidines via cycloisomerization of N-tethered 1,6-enynes
Wang, Jianping,Xie, Xiaomin,Ma, Fangfang,Peng, Zhiyong,Zhang, Lei,Zhang, Zhaoguo
experimental part, p. 4212 - 4217 (2010/07/05)
A rhodium-catalyzed cycloisomerization reaction of N-tethered 1,6-enynes with an intramolecular halogen shift has been developed, providing a useful process for the synthesis of stereo defined γ-butyrolactam and pyrrolidine derivatives in good to excellent yields. Effects of both electronic feature and steric structure of the substrates on the outcome of the reaction were investigated.
Catalytic dicyanative [4 + 2] cycloaddition triggered by cyanopalladation using ene-enynes and cyclic enynes with methyl acrylate
Arai, Shigeru,Koike, Yuka,Hada, Hirohiko,Nishida, Atsushi
supporting information; experimental part, p. 7573 - 7579 (2011/02/25)
Palladium-catalyzed dicyanative [4 + 2] cycloaddition using various ene-enynes was investigated. The key species in this process is a cyanoallene intermediate that is obtained by the cyanopalladation of conjugated enynes followed by 5-exo-cyclization. To
Stereocontrolled preparation of bicyclic alkaloid analogues: an approach towards the kinabalurine skeleton
Kavanagh, Yvonne,O'Brien, Matthew,Evans, Paul
experimental part, p. 8259 - 8268 (2009/12/24)
An approach towards the construction of bicyclic analogues of monoterpene alkaloids belonging to the kinabalurine, incarvilline and skytanthine families of natural products is reported. These syntheses rely on a stereoselective intramolecular Pauson-Khand
Cycloisomerization of 1,6-enynes using acetate as a nucleophile under palladium (II) catalysis
Zhang, Qinghai,Xu, Wei,Lu, Xiyan
, p. 1505 - 1507 (2007/10/03)
(Chemical Equation Presented) An efficient method for the synthesis of five-membered carbo- and heterocyclic compounds, including fused rings, was reported using acetate as a nucleophile in the cyclization of 1,6-enynes under palladium(II) catalysis. The
Silicon-initiated carbonylative carbotricyclization and [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes
Bennacer, Bibia,Fujiwara, Masaki,Lee, Seung-Yub,Ojima, Iwao
, p. 17756 - 17767 (2007/10/03)
The reaction of dodec-11-ene-1,6-diynes or their heteroatom congeners with a hydrosilane catalyzed by Rh(acac)(CO)2 at ambient temperature and pressure of CO gives the corresponding fused 5-7-5 tricyclic products, 5-oxo-1,3a,4,5,7,9-hexahydro-3
Synthesis of aromatic triynes as precursors to helicene derivatives
Stara, Irena G.,Kollarovic, Adrian,Teply, Filip,Stary, Ivo,Saman, David,Fiedler, Pavel
, p. 577 - 609 (2007/10/03)
A general and versatile synthetic approach to a broad series of aromatic triynes as precursors to helicene derivatives has been developed. Employing a set of simple tools, triynes comprising the (phenylethynyl)benzene, 1-(phenylethynyl)naphthalene, and 1-(1-naphthylethynyl)-naphthalene moiety have been prepared in good to excellent yields throughout the whole reaction sequence. The methodology allows constructing various types of a junction between the central diarylacetylene moiety and the attached acetylene units to get the target triynes of general formula R-C≡C-CH2-X-CH2-Ar-C≡C-Ar-CH 2-X-CH2-C≡C-R or R-C≡C-CH2CH2-Ar-C=C-Ar-CH2CH 2-C≡C-R (R = H, CH3, TMS, or TIPS; X = O, NTs, or C(CO2CH3)2; Ar/Ar = 2-phenylene or 2-naphthylene).
