37830-01-6Relevant academic research and scientific papers
Catalytic Enantioselective Synthesis of Halocyclopropanes
Pons, Amandine,Ivashkin, Pavel,Poisson, Thomas,Charette, André B.,Pannecoucke, Xavier,Jubault, Philippe
supporting information, p. 6239 - 6242 (2016/05/02)
A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2-haloalkenes with tert-butyl α-cyano-α-diazoacetate using a chiral rhodium catalyst that permits access to a broad range
2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF
Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
supporting information; experimental part, p. 1380 - 1382 (2010/09/05)
An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.
Convenient divergent strategy for the synthesis of TunePhos-type chiral diphosphine ligands and their applications in highly enantioselective Ru-catalyzed hydrogenations
Sun, Xianfeng,Zhou, Le,Li, Wei,Zhang, Xumu
, p. 1143 - 1146 (2008/09/18)
(Chemical Equation Presented) A convenient, divergent strategy for the synthesis of a series of modular and fine-tunable C3-TunePhos-type chiral diphosphine ligands and their applications in highly efficient Rucatalyzed asymmetric hydrogenations were explored. Up to 97 and 99% ee values were achieved for the enantioselective synthesis of β-methyl chiral amines and α-hydroxy acid derivatives, respectively.
Enantioselective hydrogenation of allylphthalimides: An efficient method for the synthesis of β-methyl chiral amines
Wang, Chun-Jiang,Sun, Xianfeng,Zhang, Xumu
, p. 4933 - 4935 (2007/10/03)
(Chemical Equation Presented) High yields and up to 98% ee have been achieved by asymmetric hydrogenation of allylphthalimides followed by hydrolysis to give β-methyl chiral amines by using a Ru-C3-tunephos catalyst (see scheme). The synthetic utility of this procedure has been demonstrated through the synthesis of the key intermediate of the LTs receptor antagonist (Zeneca ZD 3532).
Use of Chloroalkenylamines for the Synthesis of 1-Azabicyclooctane and 1-Azabicyclononane Derivatives
Lochead, Alistair W.,Proctor, George R.,Caton, Michael P. L.
, p. 2477 - 2489 (2007/10/02)
Various N-(chloroprop-2-enyl)-, N-(3-chlorobut-2-enyl)-, N-(4-chloropent-3- and -4-enyl)-proline derivatives, -succinimides, and -phthalimides have been synthesised and subjected to Lewis acid treatment.The following gave fruitful results: N-(4-chloropent-3-enyl)-5-hydroxy-2-pyrrolidone (25) gave 1-acetyl-1,2,3,6,7,7a-hexahydropyrrolizin-5-one (28); N-(4-chloropent-3-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (30) gave 1-endo-acetyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (31) which was isomerised to the exo-isomer; N-(4-chloropent-3-enyl)-3-methylene-2,3-dihydro- 1H-isoindol-1-one (34) and N-(4-chloropent-3-enyl)-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one (33) gave 1-endo-acetyl-9b-methyl-1,2,3,9b-tetrahydropyrroloisoindol-5-one (35); N-proline (42) gave 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrroloisoquinoline (43), N-(2-chloroprop-2-enyl)-2-(2-hydroxy-2-propyl)pyrrolidine (44) gave 6-chloro-8,8-dimethyl-1,2,3,5,8,8a-hexahydroindolizine (47) and 8,8-dimethyl-1,2,3,7,8,8a-hexahydroindolizin-6(5H)-one (48) which were reduced to the corresponding alcohols; N-(4-chloropent-4-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (50) gave 7,8,11,11a-tetrahydro-5H-azepinoisoindole-5,10(9H)-dione (51).
