179923-30-9Relevant academic research and scientific papers
Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group
Tian, Duanshuai,Li, Chengxi,Gu, Guoxian,Peng, Henian,Zhang, Xumu,Tang, Wenjun
supporting information, p. 7176 - 7180 (2018/05/29)
Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB1 receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.
Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330
Stella, Selvaraj,Chadha, Anju
, p. 345 - 352 (2013/01/15)
Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.
Asymmetric aerobic oxidation of α-hydroxy acid derivatives catalyzed by reusable, polystyrene-supported chiral N-salicylidene oxidovanadium tert-leucinates
Salunke, Santosh B.,Babu, N.Seshu,Chen, Chien-Tien
, p. 1234 - 1240 (2011/06/26)
The direct immobilization of two different C-5-propargyl ether-modified, chiral N-salicylidene vanadyl(V) tert-leucinates onto 4-azidomethyl-substituted polystyrene by click chemistry was examined. Among the eight different solvents investigated, the resulting polystyrene-supported catalysts promote the asymmetric, aerobic oxidation of α-hydroxy (thio)esters and amides with enantioselectivities of up to 99% ee (selectivity factor up to 41) in chloroform. These polystyrene-supported catalysts can be readily recovered by filtration and reused for at least four consecutive runs without discernible loss of reactivity and enantioselectivity.
Synthetic antineoplastic agents derived from dolastatin 15 and methods of making same
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Page column 5, (2008/06/13)
A composition of matter, denominated herein as 12a-r, having the structural formula set forth below: wherein R is selected from the group consisting of: a) R=NHPh; b) R=NHCH2Ph; c) R=NH(CH2)2Ph; d) R=NH(CH2)sub
Modular evolution of a chiral auxiliary for the 1,3-dipolar cycloaddition of isomuenchnones with vinyl ethers.
Savinov, Sergey N,Austin, David J
, p. 1415 - 1418 (2007/10/03)
[reaction: see text]. The 1,3-dipolar cycloaddition reaction has long been recognized as a powerful methodology in organic synthesis. More recently, this reaction has become a popular manifold for the construction of chemical diversity. Herein, we report the development of a chiral template for the facially selective cycloaddition of isomuenchnones, a common class of 1,3-dipoles. The modular format of the asymmetric unit allowed a systematic optimization of selectivity. In addition, the chiral auxiliary was removed through an unusually facile ester aminolysis.
