112393-89-2Relevant academic research and scientific papers
Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis
Biswas, Souvagya,Kubota, Koji,Orlandi, Manuel,Turberg, Mathias,Miles, Dillon H.,Sigman, Matthew S.,Toste, F. Dean
supporting information, p. 589 - 593 (2018/02/21)
Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes the direct oxidation of sulfides to a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition to form chiral cyclic N,S-acetals with moderate to high enantioselectivites. Deuterium-labelling experiments were performed to identify the stereodiscrimination step of this process. Further analysis of the reaction transition states, by means of multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.
A new strategy for the synthesis of β-benzylmercaptoethylamine derivatives
Ghosh, Subrata,Tochtrop, Gregory P.
supporting information; experimental part, p. 1723 - 1726 (2009/07/05)
Here, we describe a new experimental approach to the synthesis of the β-benzylmercaptoethylamine functionality, and illustrate its synthetic utility in multi-component reactions. Although prevalent in modern organic synthesis, no general methods have been described for this functionality. Using a carefully developed LiOH-water-ethanol reaction mixture, we were able to produce a diverse collection of β-benzylmercaptoethylamines containing a range of sensitive functional groups in excellent yields. To further illustrate their utility in molecular library synthesis, we also report the use of β-benzylmercaptoethylamines in five different multi-component reactions.
Inhibition of 5-lipoxygenase by substituted 3,4-dihydro-2H-1,4-thiazines
Weintraub,Skoog,Nichols,Wiseman,Huber,Baugh,Farrell
, p. 937 - 943 (2007/10/02)
A series of substituted 3,4-dihydro-2H-1,4-thiazines inhibit 5-lipoxygenase from rat leukocytes and exhibit submicromolar IC50 values. A novel synthesis of these compounds was developed based on the formation of hydroxymethyleneamine 13 and its
HETEROCYCLES. 11. SULFUR ANALOGS OF 3-(3-HYDROXYPHENYL)-N-n-PROPYLPIPERIDINE
Weintraub, Philip M.,Miller, Frank P.,Wiech, Norbert L.
, p. 1503 - 1516 (2007/10/02)
Analogs of 3-(3-hydroxyphenyl)-N-n-propylpiperidine (3-PPP) and 3-(3-hydroxyphenyl)-N-(2-phenylethyl)piperidine (phenethyl 3-PP) in which carbon 4 was replaced by sulfur were synthesized and tested for dopamine autoreceptor activity.
