90481-83-7Relevant academic research and scientific papers
Enantioselective Synthesis of Cyclohepta[ b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step
H?fner, Maximilian,Sokolenko, Yevhenii M.,Gamerdinger, Paul,Stempel, Erik,Gaich, Tanja
supporting information, p. 7370 - 7374 (2019/10/08)
An enantioselective synthesis of functionalized cyclohepta[b]indoles via Pd-catalyzed cyclopropane C-H activation followed by olefination and indole-vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta[b]indoles were accessed from a single compound exhibiting a "hidden" symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.
H-bonding vs Protonation of Alkynes in Regioselective Hydroamination Reactions: A Glimpse into the Reactivity of Arylogous Ynolethers and Ynamines
Abe, Masahiro,Jean, Alexandre,Blanchet, Jér?me,Rouden, Jacques,Maddaluno, Jacques,De Paolis, Micha?l
, p. 15448 - 15475 (2019/11/29)
In this paper is described the competition and transition between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic rings and to chiral amino ester appendages on the other side. While the first mode of activation indu
Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. Approaches to Ergot Alkaloids
Harrington, Peter J.,Hegedus, Louis S.
, p. 2658 - 2662 (2007/10/02)
An efficient synthesis of 4-bromo-1-tosylindole (10) based on the Pd(II)-catalyzed cyclization of an o-ethenylaniline p-toluenesulfonamide has been developed.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted 10 to a number of 4-substituted 1-tosylindoles.Selective electrophilic substitutions at the 3-position of 10 provided access to the 3-(chloromercurio)- (18) and 3-iodo-1-tosylindoles (22).Transmetalation to palladium and allyl chloride insertion converted 18 to 3-allyl-4-bromo-1-tosylindole (20) which could be cyclized to the benzindoline 21.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted the 3-iodo compound 22 to a number of 4-bromo-3-substituted 1-tosylindoles including 24, a potential precursor to optically active tryptophans.
