626207-42-9Relevant academic research and scientific papers
Enantio- and Regioconvergent Nickel-Catalyzed C(sp3)?C(sp3) Cross-Coupling of Allylic Electrophiles Steered by a Silyl Group
Kranidiotis-Hisatomi, Nektarios,Oestreich, Martin,Yi, Hong
supporting information, p. 13652 - 13655 (2021/05/10)
A two-step sequence for the enantio- and diastereoselective synthesis of exclusively alkyl-substituted acyclic allylic systems with a stereocenter in the allylic position is reported. The asymmetric induction and the site selectivity are controlled in an
Enantioselective Construction of α-Chiral Silanes by Nickel-Catalyzed C(sp3)?C(sp3) Cross-Coupling
Yi, Hong,Mao, Wenbin,Oestreich, Martin
supporting information, p. 3575 - 3578 (2019/02/16)
An enantioselective C(sp3)?C(sp3) cross-coupling of racemic α-silylated alkyl iodides and alkylzinc reagents is reported. The reaction is catalyzed by NiCl2/(S,S)-Bn-Pybox and yields α-chiral silanes with high enantiocontr
Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling
Cao, Qun,Howard, Joseph L.,Wheatley, Emilie,Browne, Duncan L.
supporting information, p. 11339 - 11343 (2018/08/28)
A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.
Continuous flow Negishi cross-couplings employing silica-supported: Pd-PEPPSI - IPr precatalyst
Price, Gregory A.,Bogdan, Andrew R.,Aguirre, Ana L.,Iwai, Toshiyuki,Djuric, Stevan W.,Organ, Michael G.
, p. 4733 - 4742 (2016/07/11)
The synthesis of a triethoxysilyl functionalised Pd-PEPPSI-IPr complex prepared via azide-alkyne cycloaddition is described. The complex was immobilised onto silica gel and applied as a heterogeneous catalyst in the Negishi reaction. The catalyst was active in both batch and continuous flow operation and was particularly effective for the coupling of heteroaryl chlorides. Long-term continuous flow experiments demonstrated good catalyst activity over fifteen hours.
Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling
Huang, Chung-Yang,Doyle, Abigail G.
supporting information, p. 5638 - 5641 (2015/05/20)
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.
α-1-C-Butyl-1,4-Dideoxy-1,4-Imino-L-Arabinitol as a second-Generation iminosugar-based oral α-Glucosidase inhibitor for improving postprandial hyperglycemia
Kato, Atsushi,Hayashi, Erina,Miyauchi, Saori,Adachi, Isao,Imahori, Tatsushi,Natori, Yoshihiro,Yoshimura, Yuichi,Nash, Robert J.,Shimaoka, Hideyuki,Nakagome, Izumi,Koseki, Jun,Hirono, Shuichi,Takahata, Hiroki
, p. 10347 - 10362 (2013/02/23)
We report on the synthesis and the biological evaluation of a series of α-1-C-alkylated 1,4-dideoxy-1,4-imino-l-arabinitol (LAB) derivatives. The asymmetric synthesis of the derivatives was achieved by asymmetric allylic alkylation, ring-closing metathesis, and Negishi cross-coupling as key reactions. α-1-C-Butyl-LAB is a potent inhibitor of intestinal maltase, isomaltase, and sucrase, with IC50 values of 0.13, 4.7, and 0.032 μM, respectively. Matrix-assisted laser desorption ionization time-of-flight mass spectrometric analysis revealed that this compound differs from miglitol in that it does not influence oligosaccharide processing and the maturation of glycoproteins. A molecular docking study of maltase-glucoamylase suggested that the interaction modes and the orientations of α-1-C-butyl-LAB and miglitol are clearly different. Furthermore, α-1-C-butyl-LAB strongly suppressed postprandial hyperglycemia at an early phase, similar to miglitol in vivo. It is noteworthy that the effective dose was about 10-fold lower than that for miglitol. α-1-C-Butyl-LAB therefore represents a new class of promising compounds that can improve postprandial hyperglycemia.
