109347-41-3Relevant academic research and scientific papers
Stereoselective synthesis of a: Podophyllum lignan core by intramolecular reductive nickel-catalysis
Xiao, Jian,Cong, Xiao-Wei,Yang, Gui-Zhen,Wang, Ya-Wen,Peng, Yu
, p. 2040 - 2043 (2018)
A Ni-catalyzed reductive cascade to a diastereocontrolled construction of THN[2,3-c]furan, is developed. The mild reaction conditions led to the tolerance of broad functional groups that can be placed in almost every position of this skeleton with good yields. The conformational control for the observed trans- or cis-fused selectivity during this tandem cyclization-coupling is also proposed.
Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Steeds, Hannah G.,Knowles, Jonathan P.,Yu, Wai L.,Richardson, Jeffery,Cooper, Katie G.,Booker-Milburn, Kevin I.
supporting information, p. 14330 - 14334 (2020/10/12)
A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.
Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium
Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa
, p. 5856 - 5859 (2017/11/10)
An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.
On homogeneous gold/palladium catalytic systems
Hashmi, A. Stephen K.,Lothschuetz, Christian,Doepp, Rene,Ackermann, Martin,De Buck Becker, Janosc,Rudolph, Matthias,Scholz, Christian,Rominger, Frank
, p. 133 - 147 (2012/04/10)
Two substrates containing an aryl iodide and an allenoate ester were prepared and the goldinduced cycloisomerisation to vinylgold(I) species and their proto-deauration as well as the intramolecular palladium-catalysed cross-coupling reactions were investigated. Switching to catalytic amounts of gold and palladium and stoichiometric amounts of silver did indeed furnish the product of a cycloisomerisation/ intramolecular cross-coupling. Control experiments revealed that silver cannot substitute for gold or palladium in these reactions, but a different palladium catalyst in a different oxidation state also afforded the cycloisomerisation/intramolecular crosscoupling products in only slightly reduced yields. By ICP analysis the palladium was shown to contain gold only at the sub-ppm level. This shows how carefully results obtained with such systems have to be interpreted. Then a series of allylic and benzylic o-alkynylbenzoates were investigated in gold-and palladium-catalysed reactions. For esters of benzyl alcohol and cinnamyl alcohol no palladium co-catalyst was needed for the conversion. All reagents were thoroughly checked for palladium traces by ICP analysis in order to thoroughly exclude a gold/palladium cocatalysis. Optimisation of the gold complex, counter ion and solvent showed that gold(I) isonitrile precatalysts and silver triflate as activator in dioxane are suitable to convert a number of substrates with aryl, alkyl and even cyclopropyl substituents. Crossover experiments proved an intermolecular allyl transfer.
Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature
Yan, Chang-Song,Peng, Yu,Xu, Xiao-Bo,Wang, Ya-Wen
supporting information; experimental part, p. 6039 - 6048 (2012/06/18)
A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright
Intramolecular cyclization strategies toward the synthesis of zoanthamine alkaloids
Fischer, Derek,Nguyen, Thong X.,Trzoss, Lynnie,Dakanali, Marianna,Theodorakis, Emmanuel A.
supporting information; experimental part, p. 4920 - 4923 (2011/10/05)
Stabilized 2-amino-1,3-dienes can participate in intramolecular Diels-Alder (IMDA) reactions with pendant dienophiles. We found that these dienes can be readily prepared via standard palladium-mediated coupling reactions and have comparable reactivity to
Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates
Tummatorn, Jumreang,Dudley, Gregory B.
supporting information; experimental part, p. 1572 - 1575 (2011/04/26)
Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl triflates (VATs) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cy
Intramolecular [1 + 2] and [3 + 2] cycloaddition reactions of cyclopropenone ketals
Patel, Paresma R.,Boger, Dale L.
supporting information; experimental part, p. 8527 - 8529 (2010/08/06)
The first intramolecular thermal reactions of cyclopropenone ketals are reported and the work examined substrates tethered to an electron-deficient olefin bearing a single electron-withdrawing substituent. Whereas the intermolecular variants of the reacti
Synthesis of 1-arylidene-2,3-dihydro-1H-inden-2-ols through a tandem carbopalladation/Suzuki-Miyaura sequence
Marchal, Estelle,Cupif, Jean-Fran?ois,Uriac, Philippe,van de Weghe, Pierre
, p. 3713 - 3715 (2008/09/20)
A regio- and stereoselective synthesis of arylidene indenols has been developed. The key step involves a palladium-catalyzed tandem carbocyclization/Suzuki-Miyaura sequence.
Synthesis of conformationally constrained phenylalanine analogues via 7-, 8- and 9-endo Heck cyclisations
Gibson, Susan E.,Guillo, Nathalie,Middleton, Richard J.,Thuilliez, Audrey,Tozer, Matthew J.
, p. 447 - 455 (2007/10/03)
The novel conformationally constrained phenylalanine analogues 2,3,4,5-tetrahydro-1H-3-benzazepine-2-carboxylic acid (Sic) 1, 1,2,3,4,5,6-hexahydro-3-benzazocine-2-carboxylic acid (Hic) 2 and 2,3,4,5,6,7-hexahydro-1H-3-benzazonine-2-carboxylic acid (Nic)
