190322-97-5Relevant academic research and scientific papers
Chiral NG-acylated hetarylpropylguanidine-type histamine H2 receptor agonists do not show significant stereoselectivity
Ghorai, Prasanta,Kraus, Anja,Birnkammer, Tobias,Geyer, Roland,Bernhardt, Günther,Dove, Stefan,Seifert, Roland,Elz, Sigurd,Buschauer, Armin
supporting information; experimental part, p. 3173 - 3176 (2010/09/05)
A set of chiral imidazolylpropylguanidines and 2-aminothiazolylpropylguanidines bearing NG-3-phenyl- or NG-3-cyclohexylbutanoyl residues was synthesized and investigated for histamine H2 receptor (H2R) agonism (guinea pig (gp) right atrium, GTPase assay on recombinant gp and human (h)H2R) and for hH2R selectivity compared to hH1R, hH3R and hH4R. In contrast to previous studies on arpromidine derivatives, the present investigation of acylguanidine-type compounds revealed only very low eudismic ratios (1.1-3.2), indicating the stereochemistry of the acyl moiety to play only a minor role in this series of H2R agonists.
Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α′-oxy enones
Garcia, Jesus M.,Gonzalez, Alberto,Kardak, Bharat G.,Odriozola, Jose M.,Oiarbide, Mikel,Razkin, Jesus,Palomo, Claudio
supporting information; experimental part, p. 8768 - 8771 (2009/10/01)
The copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to α'-oxy enones was investigated. Cu(OTf)2, ligand, and toluene were placed in a flame-dried Schlenk tube. the resulting mixture was stirred at room temperature f
ASYMMETRIC CONJUGATE ADDITION REACTION BY THE USE OF (S)-γ-TRITYLOXYMETHYL-γ-BUTYROLACTAM AS A CHIRAL AUXILIARY
Tomioka, Kiyoshi,Suenaga, Toshiro,Koga, Kenji
, p. 369 - 372 (2007/10/02)
(S)-γ-Trityloxymethyl-γ-butyrolactam (2) serves as a chiral auxiliary in the conjugate addition reaction of the corresponding imide (3) of α,β-unsaturated carboxylic acids with Grignard reagents in the presence of CuBr-SMe2 in THF to give, after hydrolysis, the β,β-disubstituted carboxylic acids (5) with predictable absolute configuration and high enantiomeric excess.
