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
, 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
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
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.
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
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
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
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).
