17556-67-1Relevant articles and documents
Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams
Janssen, Guido V.,van den Heuvel, Joyce A.C.,Megens, Rik P.,Benningshof, Jorg C.J.,Ovaa, Huib
, p. 41 - 49 (2018)
Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised
Isomerization and deuterium scrambling evidence for a change in the rate-limiting step during imine hydrogenation by Shvo's hydroxycyclopentadienyl ruthenium hydride
Casey, Charles P.,Johnson, Jeffrey B.
, p. 1883 - 1894 (2007/10/03)
Hydroxycyclopentadienyl ruthenium hydride 5 efficiently reduces imines below room temperature. Better donor substituents on nitrogen give rise to faster rates and a shift of the rate-determining step from hydrogen transfer to amine coordination. Reduction of electron-deficient N- benzilidenepentafluoroaniline (8) at 11°C resulted in free amine and kinetic isotope effects of kOH/kOD = 1.61 ± 0.08, k RuH/kRuD = 2.05 ± 0.08, and kRuHOH/ kRuDOD = 3.32 ± 0.14, indicative of rate-limiting concerted hydrogen transfer, a mechanism analogous to that proposed for aldehyde and ketone reduction. Reduction of electron-rich N-alkyl-substituted imine, N-isopropyl-(4-methyl)benzilidene amine (9), was accompanied by facile imine isomerization and scrambling of deuterium labels from reduction with 5-RuDOH into the N-alkyl substituent of both the amine complex and into the recovered imine. Inverse equilibrium isotope effects were observed in the reduction of N-benzilidene-tert-butylamine (11) at -48°C (kOH/kOD = 0.89 ± 0.06, kRuH/kRuD = 0.64 ± 0.05, and kRuHOH/kRuDOD = 0.56 ± 0.05). These results are consistent with a mechanism involving reversible hydrogen transfer followed by rate-limiting amine coordination.
A Convenient One-Pot Synthesis of 4-Substituted 3,5-Bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-Oxides from Aldehydes and Nitroacetic Esters in a Solid-Liquid Reaction System and Subsequent Deoxygenation
Melot, Jean-Marie,Texier-Boullet, Francoise,Foucaud, Andre
, p. 558 - 560 (2007/10/02)
4-Substituted 3,5-bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-oxides are obtained from nitroacetic esters and imines which are prepared from aldehydes and isopropylamine in the presence of molecular sieves.Reduction of the N-oxides with trimethyl phosphite
