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.
ETUDE DE LA REACTION CHLOROCARBENE-ACETALS DE CETENES. II. STEREOSELECTIVITE DE LA REACTION.
Rousseau, G.,Slougui, N.
, p. 2653 - 2664 (2007/10/02)
We have studied the stereoselectivity of the addition reaction of chloro and chloromethyl carbenoids with ketene alkylsilyl acetals.The best stereoselectivity was generally observed with the dimethyl tertiobutylsilyloxy group.With the chlorocarbenoid, using an E ketene acetal we obtained in majority (ca. 80percent) an E α,β-ethylenic ester and using a Z ketene acetal we obtained in majority (ca. 70percent) a Z α,β-ethylenic ester.In the case of the chloromethyl carbenoid the two ketene acetal isomers led to the same α-substituted α,β-ethylenic ester (ca. 88percent of selectivity).With the chlorophenylcarbenoid, formation of ca. 90percent of E α phenyl α,β-ethylenic ester is observed.
