96641-45-1Relevant academic research and scientific papers
Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives
Qu, Bo,Tan, Renchang,Herling, Madison R.,Haddad, Nizar,Grinberg, Nelu,Kozlowski, Marisa C.,Zhang, Xumu,Senanayake, Chris H.
, p. 4915 - 4920 (2019/03/19)
Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are compatible with both electron-rich and electron-poor substituents.
A straightforward organocatalytic alkylation of 2-arylacetaldehydes: An approach towards bisabolanes
Gualandi, Andrea,Canestrari, Pietro,Emer, Enrico,Cozzi, Pier Giorgio
, p. 528 - 536 (2014/05/20)
A highly stereoselective organocatalytic aalkylation of 2-arylacetaldehydes with a commercially available carbenium tetrafluoroborate is described. The stereoselective alkylation was carried out in acetonitrile/ water, under air in the presence of a commercially available imidazolidinone (MacMillan's catalyst). Key intermediates for the synthesis of bisabolanes were obtained through a simple chemistry. In particular a direct, enantioselective and facile synthesis of (R)-(-)-curcumene is described.
DNA-PK INHIBITORS
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Paragraph 0244, (2013/11/05)
The present invention relates to compounds useful as inhibitors of DNA-PK. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.
On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides
Denmark, Scott E.,Werner, Nathan S.
supporting information; experimental part, p. 3612 - 3620 (2010/05/01)
The stereochemical course of palladium-catalyzed cross-coupling reactions of an enantioenriched, a-substituted, allylic silanolate salt with aromatic bromides has been investigated. The allylic silanolate salt was prepared in high geometrical (Z/E, 94:6) and high enantiomeric (94:6 er) purity by a coppercatalyzed SN2′ reaction of a resolved allylic carbamate. Eight different aromatic bromides underwent crosscoupling with excellent constitutional site-selectivity and excellent stereospecificity. Stereochemical correlation established that the transmetalation event proceeds through a syn SE′ mechanism which is interpreted in terms of an intramolecular delivery of the arylpalladium electrophile through a key intermediate that contains a discrete Si-O-Pd linkage.
Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters
Schaefer, Carsten,Fu, Gregory C.
, p. 4606 - 4608 (2007/10/03)
(Chemical Equation Presented) With a little help from the ferrocenyl catalyst ((-)-1), a wide array of α-arylalkanoic acid derivatives can be produced from the catalytic asymmetric coupling of ketenes with aldehydes (see scheme). The enol esters are readily transformed into other useful families of compounds such as carboxylic acids and alcohols.
The Total Synthesis of (15R)- and (15S)-16-Hydroxyferruginol
Matsumoto, Takashi,Imai, Sachihiko,Miuchi, Shigekazu,Sugibayashi, Hidenori
, p. 340 - 345 (2007/10/02)
In order to assign the absolute configuration of C-15 in natural 16-hydroxyferruginol, (5S,10S,15R)-(1a) and (5S,10S,15S)-8,11,13-abietatriene-12-16-diol (1b) have been synthesized.Optical resolution of 2-(2-methoxyphenyl)propanoic acid, prepared from methyl (2-methoxyphenyl)acetate, with cinchonidine afforded (R)- and (S)-enantiomers, which were converted into triphenylphosphonium chloride (3a) and its (S)-isomer (3b) respectively.The Wittig reaction of (R)-(-)-α-cyclocitral with 3a, followed by partial catalytic hydrogenation and intramolecular cyclization gave (5S,10S,15R)-12,16-dimethoxy-8,11,13-abietatriene (16a) together with its (5S,10R,15R)-isomer.Similary, 3b was also converted into (5S,10S,15S)-12,13-dimethoxy-8,11-abietatriene (6b) and its (5S,10R,15R)-isomer.Demethylation of 16a gave 1a which was identical with natural 16-hydroxyferruginol.The dimethoxy compound 16b was also demethylated to give 1b.
