1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐Promoted Efficient and Versatile aza‐Michael Addition.

Yeom, Chang-Eun; Kim, Mi Jeong; Kim, B. Moon

doi:10.1002/chin.200721036

Cited by 9 publications

(11 citation statements)

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“…In solution, it was found that 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is a suitable catalyst for the forward aza-Michael reaction 24 and at the same time also catalyses the retro reaction 25 (see Supplementary Fig. 1 ).…”

Section: Resultsmentioning

confidence: 99%

Emergence of single-molecular chirality from achiral reactants

et al. 2014

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The synthesis of enantiopure molecules from achiral precursors without the need for pre-existing chirality is a major challenge associated with the origin of life. We here show that an enantiopure product can be obtained from achiral starting materials in a single organic reaction. An essential characteristic of this reaction is that the chiral product precipitates from the solution, introducing a crystal–solution interface which functions as an asymmetric autocatalytic system that provides sufficient chiral amplification to reach an enantiopure end state. This approach not only provides more insight into the origin of life but also offers a pathway to acquire enantiopure compounds for industrial applications.

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Section: Resultsmentioning

confidence: 99%

Emergence of single-molecular chirality from achiral reactants

et al. 2014

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“…Benzyl (2 S ,4 R )‐4‐{[ tert ‐Butyl(dimethyl)silyl]oxy}‐2‐({(2 S )‐1‐[(2‐cyanoethyl)(prop‐2‐en‐1‐yl)amino]‐1‐oxo‐4‐phenylbutan‐2‐yl}carbamoyl)pyrrolidine‐1‐carboxylate ( 22c ) was synthesized following the General Procedure from 17a (162 mg, 0.3 mmol) and 21c , obtained according to (40 mg, 0.36 mmol), affording 157 mg (82.7%) of 22c as syrup.

{false[italicα false]}_{normalD}^{27.4}

= −36.8 ( c = 0.5, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Peptidomimetic N‐Substituted Cbz‐4‐Hyp‐Hpa‐Amides as Novel Inhibitors of Plasmodium falciparum

Bacherikov

Chittiboyina

Avery

2017

Chemistry & Biodiversity

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A new series of peptidomimetic N-substituted Cbz-4-Hyp-Hpa-amides were designed, synthesized, and evaluated for inhibition of the Plasmodium falciparum. Substituents on the N-atom of the amide group were selected alkyl-, allyl-, aryl-, 2-hydroxyethyl-, 2-cyanoethyl-, cyanomethyl-, 2-hydroxyethyl-, 2,2-diethoxyethyl-, or 2-ethoxy-2-oxoethylamino groups, and about of 40 new compounds were synthesized and evaluated for antiplasmodial activity in vitro. Antimalarial activity has been investigated as for the final peptide mimetics, and their immediate predecessors, carrying TBDMS or TBDPS protecting groups on 4-hydroxyproline residue and 18 derivatives exhibited toxicity against P. falciparum. Of these agents, compound 23e was shown to have potent antimalarial activity with IC 528 ng/ml.

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“…The aza-Michael reaction has been accomplished with several additives to increase its efficiency. Among them are variety of Lewis acids such as InCl 3 , [3] Bi(NO 3 ) 2 and Bi(OTf) 2 , [4] PdCl 2 (MeCN) 2 , [5] Yb(OTf) 2 , [6] LiClO 4 , [7] FeCl 3 , [8] SmI 2 , [9] ceric ammonium nitrate, [10] stoichiometric amounts of AlCl 3 =TiCl 4 =SnCl 4 , [11] clay , [12] heterogeneous solid salts , [13] ionic liquids with Cu(acac) 2 or quaternary ammonium salts, [14] b-cyclodextrin, [15] polystyrenesulfonic acid, [16] 1,8-diazabicyclo [5.4.0]-undec-7-ene (DBU), [17] some organic promoters, [18] and sodium dodecylsulfate. [19] The use of these additives and organic solvents along with much higher reaction temperatures do not agree with the main principles of green synthesis.…”

Section: Introductionmentioning

confidence: 99%