155325-51-2Relevant academic research and scientific papers
Synthesis and evaluation of C2-symmetric bis-sulfinamides as effective ligands in rhodium catalyzed addition of arylboronic acids to cycloalkenones
Revu, Omkar,Uphade, Manoj B.,Prasad, Kavirayani R.
, p. 5355 - 5362 (2016)
Synthesis of novel C2-symmetric 1,2- 1,3- and 1,4- bis-sulfinamides and their use as effective ligands in rhodium (I) catalyzed asymmetric conjugate addition of arylboronic acids to cyclohexenone and cyclopentenones is described. C2-
Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?
Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu
supporting information, p. 933 - 936 (2021/03/03)
The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.
Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones
Yuan, Shuai,Zeng, Qingle,Wang, Jiajun,Zhou, Lihong
supporting information, p. 32 - 42 (2021/02/09)
Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1
Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions
Bieliūnas, Vidmantas,Ston?ius, Sigitas
, p. 3815 - 3823 (2021/07/28)
Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.
Synthesis of Highly Enantioenriched Propelladienes and their Application as Ligands in Asymmetric Rh-Catalyzed 1,4-Additions
Pecchioli, Tommaso,Christmann, Mathias
supporting information, p. 5256 - 5259 (2018/09/13)
The first synthesis of highly enantioenriched [4.3.3]propelladienes is reported. The novel bridged bicyclo[3.3.0] dienes were applied as steering ligands in the rhodium-catalyzed asymmetric arylation of cyclic enones. The catalytic system showed high catalytic activity, and the 1,4-adducts were obtained in good to excellent yields (46-99%) with enantioselectivities up to 96% ee.
A New Type of Chiral Cyclic Sulfinamide–Olefin Ligands for Rhodium-Catalyzed Asymmetric Addition
Wen, Quan,Zhang, Li,Xiong, Jing,Zeng, Qingle
supporting information, p. 5360 - 5364 (2016/11/22)
A new type of chiral cyclic sulfinamide–olefin ligands, N-allylic 2,3-dihydro-1,2-benzoisothiazole 1-oxides, with 2,3-dihydro-1,2-benzoisothiazole 1-oxide as a unique chiral skeleton, is developed for the highly enantioselective rhodium-catalyzed asymmetr
Stereoselective Synthesis of 3-Hydroxy-4-arylcyclopentanones and 4-Arylcyclopentenones through a Heck-Matsuda Desymmetrization of meso cis-4-Cyclopentene-1,3-diol
Carmona, Rafaela C.,Correia, Carlos Roque D.
supporting information, p. 2639 - 2643 (2015/09/01)
A new palladium-catalyzed route to 3-hydroxy-4-arylcyclopentanones and 4-arylcyclopentenones in a diastereo- and enantioselective manner by a Heck-Matsuda desymmetrization was achieved from the commercially available meso cis-4-cyclopentene-1,3-diol. This method is highly practical, mild, high yielding and is carried out under "open vessel" conditions. Protected and unprotected substrates provide distinct products bearing considerable value as synthetic scaffolds for the synthesis of natural and unnatural bioactive compounds containing a five-membered ring.
4,8-disubstituted bicyclo[3.3.1]nona-2,6-dienes as chiral ligands for rh-catalyzed asymmetric 1,4-addition reactions
Rimkus, Renaldas,Jurgelenas, Marius,Ston?ius, Sigitas
supporting information, p. 3017 - 3021 (2015/05/13)
C2-symmetric chiral diene ligands based on 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene framework have been designed and synthesized. The rhodium complexes of the dienes, which were obtained in a few straightforward steps from enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione, exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) in the conjugate addition reaction of arylboronic acids to cyclic enones under mild reaction conditions with high atom efficiency. Chiral C2-symmetric 4,8-endo,endo-disubstituted bicyclo[3.3.1]nona-2,6-diene ligands were synthesized from easily available bicyclo[3.3.1]nonane-2,6-dione and utilized in the asymmetric 1,4-addition reaction of arylboronic acids to cyclic enones. The catalyst prepared in situ from ligand 4b and [RhCl(C2H4)2]2 exhibited excellent catalytic activity and high enantioselectivity (up to 96% ee) under mild reaction conditions with high atom efficiency.
Stereoselective Synthesis of Aryl Cyclopentene Scaffolds by Heck-Matsuda Desymmetrization of 3-Cyclopentenol
Angnes, Ricardo A.,Oliveira, Juliana M.,Oliveira, Caio C.,Martins, Nelson C.,Correia, Carlos Roque D.
, p. 13117 - 13121 (2015/10/20)
A new enantioselective Heck-Matsuda desymmetrization reaction was accomplished by using 3-cyclopentenol to produce chiral five-membered 4-aryl cyclopentenol scaffolds in good yields and high ee's, together with some 3-aryl-cyclopentanones as minor products. Mechanistically, the hydroxyl group of 3-cyclopentenol acts as a directing group and is responsible for the cisarrangement in the formation of the 4-aryl-cyclopentenols.
Design and synthesis of polymeric chiral bicyclo[3.3.0] diene as reusable ligand for rhodium-catalyzed asymmetric 1,4-addition
Yang, Hongyu,Xu, Minghua
supporting information, p. 119 - 122 (2013/08/24)
A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. With polymeric diene 6b, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. A series of A-B type sterically regular bicyclio[3.3.0] diene-based polymers were designed and synthesized as immobilized chiral diene ligands for asymmetric catalysis. By using polymeric diene, good to excellent enantioselectivities can be achieved in Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated ketones. Copyright
