78776-45-1Relevant academic research and scientific papers
Sustainable Pd(OAc)2/Hydroquinone Cocatalyst System for Cis-Selective Dibenzoyloxylation of 1,3-Cyclohexadiene
Borovika, Alina,Eastgate, Martin D.,Fraunhoffer, Kenneth J.,Geng, Peng,Schmidt, Michael A.,Stahl, Shannon S.,Stamoulis, Alexios G.
supporting information, p. 23182 - 23186 (2021/09/20)
The 1,4-diacyloxylation of 1,3-cyclohexadiene (CHD) affords valuable stereochemically defined scaffolds for natural product and pharmaceutical synthesis. Existing cis-selective diacyloxylation protocols require superstoichiometric quantities of benzoquino
Pd-Catalyzed Asymmetric Allylic Substitution Annulation Using Enolizable Ketimines as Nucleophiles: An Alternative Approach to Chiral Tetrahydroindoles
Xu, Kai,Ye, Jianxun,Liu, Hao,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin
supporting information, p. 2059 - 2069 (2020/04/29)
A synthesis of chiral tetrahydroindoles has been developed via a Pd-catalyzed asymmetric allylic substitution annulation using unstable enolizable ketimines as nucleophiles and our previously developed tBu-RuPHOX as a chiral ligand. The reaction proceeds via an asymmetric desymmetrization of the meso-diacetatecycloalkenes, providing the desired chiral tetrahydroindoles in moderate to good yields and with up to 96% ee. The annulation reaction could be performed on a gram-scale in high yields and the resulting products can be transformed to several types of N-hetereobicyclic derivatives. In addition, a chiral cis-perhydroindolic acid derivative was also readily synthesized starting from a prepared chiral tetrahydroindole. (Figure presented.).
The construction of chiral fused azabicycles using a Pd-catalyzed allylic substitution cascade and asymmetric desymmetrization strategy
An, Qianjin,Liu, Delong,Shen, Jiefeng,Liu, Yangang,Zhang, Wanbin
supporting information, p. 238 - 241 (2017/11/27)
A highly enantioselective Pd-catalyzed asymmetric allylic substitution cascade of cyclic N-sulfonylimines with an accompanying asymmetric desymmetrization has been developed for the construction of fused tetrahydroindole derivatives bearing two chiral centers. Mechanistic studies confirmed that the cascade reaction proceeds by initial allylic alkylation and subsequent allylic amination. The first alkylation is a chirality-control step and represents an asymmetric desymmetrization of ciscyclic allyl diacetates. The reaction has been performed on a gram scale, and the desired products can take part in several transformations.
Synthesis of branched carbasugars via photooxygenation and manganese(III) acetate free radical cyclization
Altun, Yasemin,Dogan, Sengul Dilem,Balci, Metin
, p. 4884 - 4890 (2014/07/07)
Transformation of cyclohexa-1,3- and 1,4-dienes to carbasugars is described. Photooxygenation of dienes gave bicyclic endoperoxides, which were reduced with thiourea to the corresponding 1,4-diols with cis-configuration. Lactonization of the remaining dou
Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration
Shiramizu, Mika,Toste, F. Dean
supporting information, p. 12905 - 12909 (2014/01/06)
New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright
Pd-catalyzed allylic alkylation cascade with dihydropyrans: Regioselective synthesis of furo[3,2- c ]pyrans
Bartlett, Mark J.,Turner, Claire A.,Harvey, Joanne E.
supporting information, p. 2430 - 2433 (2013/07/05)
A regioselective palladium-catalyzed allylic alkylation cascade forms furo[3,2-c]pyrans from various cyclic β-dicarbonyl bis-nucleophiles and 3,6-dihydro-2H-pyran bis-electrophiles. The combination of allylic carbonate and anomeric siloxy leaving groups in the dihydropyran substrate allows control of the many regiochemical possibilities in this reaction. Annulation proceeds stereoconvergently to give cis-fused furopyrans from either cis- or trans-substituted starting material.
The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties
Arthurs, Claire L.,Morris, Gareth A.,Piacenti, Michela,Pritchard, Robin G.,Stratford, Ian J.,Tatic, Tanja,Whitehead, Roger C.,Williams, Katharine F.,Wind, Natasha S.
experimental part, p. 9049 - 9060 (2011/01/04)
The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A, are described. The target structures were selected in order to probe the influence of several key structural parameters on in vi
Synthesis of 2-ene-1,4-diols by a new cascade-opening of 1,3-diepoxides: Towards an efficient synthesis of dihydroxytaxoid derivatives
Aldegunde, Maria J.,Castedo, Luis,Granja, Juan R.
supporting information; experimental part, p. 4785 - 4787 (2009/12/09)
The synthesis of dihydroxytaxoid derivatives, specially 2-Ene-1,4-diols using a new cascade-opening of 1,3-diepoxides was investigated. The study prepared a framework through a cascade ring-closing dienyne metathesis (RCDEYM) reaction from Dienyne. The me
Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties
Arthurs, Claire L.,Wind, Natasha S.,Whitehead, Roger C.,Stratford, Ian J.
, p. 553 - 557 (2007/10/03)
The syntheses of three novel analogues of the naturally occurring cytotoxic agent COTC are described and the results of bioassays of the target compounds against two lung cancer cell lines are presented.
Fast and mild palladium(II)-catalyzed 1,4-oxidation of 1,3-dienes via activation of molecular oxygen with a designed cobalt(II) porphyrin
Verboom, Renzo C.,Slagt, Vincent F.,Baeckvall, Jan-E.
, p. 1282 - 1284 (2008/09/16)
The use of a Co(porphyrin)-amide ligand, 2, in the palladium(II)-catalyzed 1,4-diacetoxylation of conjugated dienes under O2 results in aerobic oxidation. The catalyst was highly active under O2, and the 1,4-diacetoxylation reaction
