705-95-3Relevant academic research and scientific papers
Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst
Adamson, Nathan J.,Hull, Ethan,Malcolmson, Steven J.
, p. 7180 - 7183 (2017/06/05)
We report a method for the catalytic, enantioselective intermolecular addition of aliphatic amines to acyclic 1,3-dienes. In most cases, reactions proceed efficiently at or below room temperature in the presence of 5 mol % of a Pd catalyst bearing a PHOX ligand, generating allylic amines in up to 97:3 er. The presence of an electron-deficient phosphine within the ligand not only leads to a more active catalyst but also is critical for achieving high site selectivity in the transformation.
Monodisperse amorphous CuB23 alloy short nanotubes: Novel efficient catalysts for Heck coupling of inactivated alkyl halides and alkenes
Yang, Fan,Fu, Shi Yan,Chu, Wei,Li, Chun,Tong, Dong Ge
, p. 45838 - 45843 (2015/02/19)
Heck-type coupling of inactivated alkyl halides and alkenes, catalyzed by amorphous CuB23 alloy short nanotubes, has been developed. Such couplings occur on the surfaces of nanotubes via a single-electron oxidative reaction. The results indicate that CuB23 nanotubes are efficient catalysts to replace Pd and Ni complexes for such Heck-type coupling. This journal is
Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: The key role of acetonitrile as a ligand
Malkov, Andrei V.,Derrien, Nolwenn,Barlog, Maciej,Kocovsky, Pavel
supporting information, p. 4542 - 4547 (2014/05/06)
A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of the Pd0 complex to Pd II and prevents double carbonylation. Acetonitrile is the key! A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates (see scheme). Key features are the use of MeCN as a solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of Pd0 to PdII and prevents double carbonylation.
Chiral magnesium(II) binaphtholates as cooperative bronsted/lewis acid-base catalysts for the highly enantioselective addition of phosphorus nucleophiles to α,β-unsaturated esters and ketones
Hatano, Manabu,Horibe, Takahiro,Ishihara, Kazuaki
supporting information, p. 4549 - 4553 (2013/06/04)
A little cooperation goes a long way: The cooperative Bronsted/Lewis acid-base supramolecular catalysts formed in situ from simple chiral magnesium(II) binaphtholate aqua complexes promoted the highly enantioselective 1,4-hydrophosphinylation of α,β-unsaturated esters with diaryl phosphine oxides and 1,2-hydrophosphonylation of α,β-unsaturated ketones with dialkyl phosphites (see scheme). Copyright
Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5- dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist
Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Murota, Masayuki,Takaoka, Yoshikazu,Nakai, Hisao,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki
experimental part, p. 4028 - 4042 (2011/08/21)
Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented.
Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate
Nishizawa, Rena,Nishiyama, Toshihiko,Hisaichi, Katsuya,Minamoto, Chiaki,Matsunaga, Naoki,Takaoka, Yoshikazu,Nakai, Hisao,Jenkinson, Stephen,Kazmierski, Wieslaw M.,Tada, Hideaki,Sagawa, Kenji,Shibayama, Shiro,Fukushima, Daikichi,Maeda, Kenji,Mitsuya, Hiroaki
scheme or table, p. 1141 - 1145 (2011/04/16)
Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compo
Investigations on the Selectivity of the β-Scission of Alkyl-Radicals, II - Selectivity of the β-Fragmentation of α-(Methoxycarbonyl)alkyl Radicals
Metzger, Juergen O.,Klenke, Kurt
, p. 875 - 879 (2007/10/02)
The rate of β-scission of α-(methoxycarbonyl)alkyl radicals 3 and 9, generated by addition of cycloalkyl radicals to appropriate methyl 2-methylenealkanoates 1 and methyl (E)-2-alkenoates 8, resp., has been measured relative to the hydrogen transfer from cycloalkanes.The rate of β-scission increases with increasing stability of the leaving radical R*.Polar effects reversing the stability sequence have also been observed, e.g. the more stable (methoxycarbonyl)methyl radical leaves more slowly than a less stable secondary alkyl radical.
GENERATION AND SYNTHETIC USE OF ALKYL RADICALS WITH 2 AS MEDIATOR
Thoma, Gebhard,Giese, Bernd
, p. 2907 - 2910 (2007/10/02)
Irradiation of dimeric iron complex 1 in the presence of alkyl halides yields alkyl radicals that are useful in organic synthesis.
Electron-transfer processes. 43. Attack of alkyl radicals upon 1-alkenyl and 1-alkynyl derivatives of tin and mercury
Russell, Glen A.,Ngoviwatchai, Preecha,Tashtoush, Hasan I.
, p. 696 - 702 (2008/10/08)
Alkyl radicals, obtained by reaction of Bu3Sn? or ClHg? with alkylmercury halides, will undergo regioselective and in some cases stereospecific substitution by a free radical chain addition-elimination mechanism with 1-alkenylstannanes or -mercurials. The chain reaction is also observed for 1-alkynyl derivatives and in the photostimulated demercuration of mixed alkyl and 1-alkenyl- or 1-alkynylmercurials. Chain propagation with alkyl radical formation is also observed to occur in the reactions of β-eliminated ClHg? with Grignard reagents in PhH-THF solution. In competitive reactions of Bu3Sn? or ClHg? with pairs of alkylmercury chlorides, it is observed that a tert-butylmercurial is >1000 times more reactive than a n-butylmercurial, suggesting a concerted dissociate electron-transfer process not involving the intermediacy of RHg? species.
