- Organocatalytic Gram-Scale Synthesis and Alkylation of Heteroaryl and Electron-Rich Aryl α-Substituted γ-Lactones
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The synthesis of γ-lactones α-substituted with heterocycles and electron-rich aromatic rings is described. The method, based on a sequence involving an organocatalytic addition of boronic acid to the 5-hydroxyfuran-2(5 H)-one, followed by reduction and lactonization, gives access to broad range of γ-lactones on a gram scale. Among these, γ-lactones bearing a benzofuran, a benzothiophene, and an indole ring were alkylated in mild catalytic conditions to construct α-quaternary stereocenters. Interesting mild oxidation reaction, using molecular oxygen, was also highlighted during this study.
- Bos, Maxence,Buttard, Floris,Riguet, Emmanuel,Vallée, Alexis
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p. 3151 - 3159
(2019/08/07)
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- Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides
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A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.
- Gao, Mengyu,Sun, Deli,Gong, Hegui
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supporting information
p. 1645 - 1648
(2019/03/11)
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- SERINE/THREONINE KINASE INHIBITORS
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Compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such diseases, or associated pathological conditions are disclosed.
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Paragraph 00263
(2015/07/16)
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- Weak arene C-h×××o hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones
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Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH×××O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH×××O hydrogen bonding to guide stereoselection. Copyright
- Huang, Zhiyan,Chen, Zuliang,Lim, Li Hui,Quang, Gia Chuong Phan,Hirao, Hajime,Zhou, Jianrong
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supporting information
p. 5807 - 5812
(2013/07/05)
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- Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis
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A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.
- Birrell, James A.,Desrosiers, Jean-Nicolas,Jacobsen, Eric N.
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supporting information; experimental part
p. 13872 - 13875
(2011/10/09)
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- Regioselective hydroformylation of allylic alcohols
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A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.
- Lightburn, Thomas E.,De Paolis, Omar A.,Cheng, Ka H.,Tan, Kian L.
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supporting information; experimental part
p. 2686 - 2689
(2011/06/28)
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- Catalytic hydrogenation of carboxamides and esters by well-defined Cp*Ru complexes bearing a protic amine ligand
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A novel catalytic method for the straightforward hydrogenation of carboxamides and esters to primary alcohols has been developed. Chiral modification in the ligand sphere of the well-defined Cp*Ru catalyst molecule opens up a new possibility for the development of an enantioselective hydrogenation of racemic substrates via dynamic kinetic resolution.
- Ito, Masato,Ootsuka, Takashi,Watari, Ryo,Shiibashi, Akira,Himizu, Akio,Ikariya, Takao
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supporting information; experimental part
p. 4240 - 4242
(2011/06/21)
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- A novel estrogen receptor ligand template
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Three synthetic routes towards a novel estrogen receptor ligand template based on a rigid bicyclo-[3.3.1]-nonene core have been investigated. The prototype compound exhibits potent binding at the ERβ receptor and promising estrogen receptor subtype select
- Sibley, Robert,Hatoum-Mokdad, Holia,Schoenleber, Robert,Musza, Laszlo,Stirtan, William,Marrero, Diana,Carley, William,Xiao, Hong,Dumas, Jacques
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p. 1919 - 1922
(2007/10/03)
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