194869-12-0Relevant academic research and scientific papers
Synthesis of annulated 1,4-dioxanes and perhydro-1,4-oxazines by domino-wacker-carbonylation and domino-wacker-mizoroki-heck reactions
Tietze, Lutz F.,Heins, Arne,Soleiman-Beigi, Mohammad,Raith, Christian
experimental part, p. 1123 - 1146 (2010/10/20)
Palladium(II) -catalyzed domino reactions for the formation of 1,4-dioxanes and perhydro-1,4-oxazines starting from hydroxy alkenes are described. The domino-Wacker-carbonylation comprises a Wacker oxidation, subsequent CO-insertion and a nucleophilic substitution of the intermediately formed Pd-species. The domino-Wacker-Mizoroki-Heck reaction proceeds via a Wacker oxidation, subsequent insertion into the olefinic π-bond of α,β-unsatura-ted carbonyl compounds and β-hydride elimination.
Synthesis of 2,3-dihydrobenzo[1,4]dioxins and -oxazins via a domino wacker-heck reaction
Tietze, Lutz F.,Wilckens, Kristina F.,Yilmaz, Sinem,Stecker, Florian,Zinngrebe, Julia
, p. 309 - 319 (2008/04/18)
An efficient and operationally simple domino Wacker-Heck reaction of allylic phenols and,-unsaturated ketones as well as esters in the presence of catalytic amounts of Pd(TFA)2 and an oxidant for the synthesis of 2,3-dihydro-benzo[1,4]dioxins and 2,3-dihydrobenzo[1,4]oxazins is described. The necessary substrates are prepared by monoallylation of catechol derivatives and ortho-aminophenol.
Chiral relay effect: 4-substituted 1,3-benzoxazol-2-(3H)-ones as achiral templates for enantioselective Diels-Alder reactions
Quaranta, Laura,Corminboeuf, Olivier,Renaud, Philippe
, p. 39 - 41 (2007/10/03)
(matrix presented) A new strategy to control the enantioselectivity of Lewis acid catalyzed reactions has been investigated. The use of N-acryloyl-1,3-benzoxazol-2-(3H)-ones substituted at position 4 leads to the formation of diastereomeric complexes as a
General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety
Kondo, Yoshinori,Kojima, Satoshi,Sakamoto, Takao
, p. 6507 - 6511 (2007/10/03)
Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.
