260413-67-0Relevant academic research and scientific papers
Alkene-directed N-attack chemoselectivity in the gold-catalyzed [2+2+1]-annulations of 1,6-enynes with N-hydroxyanilines
Huple, Deepak B.,Mokar, Bhanudas D.,Liu, Rai-Shung
supporting information, p. 14924 - 14928 (2016/02/05)
Kinetically unstable nitrones are generated from gold-catalyzed reactions of 1,6-enynes with N-hydroxyanilines, and subsequently trapped by tethered alkenes to furnish [2+2+1]-annulations. Our experimental data reveal that such nitrones arise from atypical N-attack chemoselectivity that is triggered by tethered alkenes to facilitate the key protodeauration reaction. Kinetically unstable nitrones are generated from gold-catalyzed reactions of 1,6-enynes with N-hydroxyanilines, and subsequently trapped by tethered alkenes to furnish [2+2+1]-annulations. These findings open the door to new ways to access ketone nitrones with good stereoselectivity.
Unexpected Pd-catalyzed coupling, propargyl-allenyl isomerization and Alder-ene reaction: Facile synthesis of some not readily available 2,3-dihydrofuran derivatives
Shen, Ruwei,Zhu, Shugao,Huang, Xian
supporting information; experimental part, p. 4118 - 4123 (2009/09/25)
(Chemical Equation Presented) An interesting sequential reaction involving Pd-catalyzed coupling, propargyl-allenyl isomerization, and Alder-ene cycloaddition is reported, providing a facile synthesis of some not readily available 2,3-dihydrofurans from e
Synthesis, structure and emission properties of spirocyclic benzofuranones and dihydroindolones: A domino insertion-coupling-isomerization-Diels-Alder approach to rigid fluorophores
D'Souza, Daniel M.,Kiel, Alexander,Herten, Dirk-Peter,Rominger, Frank,Mueller, Thomas J. J.
, p. 529 - 547 (2008/12/22)
An alkynoyl ortho-iodo phenolester or alkynoyl ortho-iodo anilides and propargyl allyl ethers react under Sonogashira coupling conditions in the sense of an insertion-coupling-isomerization-Diels-Alder hetero domino reaction to furnish (tetrahydroisobenzo
Mechanistic dichotomy in CpRu(CH3CN)3PF6 catalyzed enyne cycloisomerizations
Trost, Barry M.,Toste, F. Dean
, p. 5025 - 5036 (2007/10/03)
Enynes are easily accessible building blocks as a result of the rich chemistry of alkynes and thus represent attractive substrates for ring formation, A ruthenium catalyst for cycloisomerization effects such reaction of 1,6- and 1,7-enynes typically at room temperature in acetone or DMF under neutral conditions. The reaction is effective for forming five- and six-membered rings of widely divergent structure. The alkyne may bear both election-donating and election-withdrawing substituents. The alkene may be di- or trisubstituted. Introduction of a quaternary center at the propargylic position of an ynoate, however, completely changes the nature of the reaction. In the case of a 1,6-enynoate, a seven-membered ring forms in excellent yield under equally mild conditions. Evidence is presented to indicate a complete change in mechanism. In the former case, the reaction involves the intermediacy of a ruthenacyclopentene. In the latter case, a C-H insertion to form a π-allylruthenium intermediate is proposed and supported by deuterium-labeling studies. A rationale is presented for the structural dependence of the mechanism.
