Nonpeptide GPIIB/IIIA receptor antagonists. Part 21: C-6 flexibility and amide bond orientation are important factors in determining the affinity of compounds for activated or resting platelet receptors

An easy and affordable route for obtaining chiral beta-aminated- and alpha,beta-diaminated aldehydes, 1,3-aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine (S)-2-[bis(3,5-bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate alpha,beta-unsaturated aldehydes, which allows succinimide to add in a 1,4-regio- and stereoselective fashion thereby forming N-protected 1,3-aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.

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Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Jiang

Nielsen

et al. 2007

Chemistry A European J

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Covalent chloramine inhibitors of blood platelet functions: Computational indices for their reactivity and antiplatelet activity

Roshchupkin

Murina²,

Сергиенко³

2011

BIOPHYSICS

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Nonpeptide GPIIB/IIIA receptor antagonists. Part 21: C-6 flexibility and amide bond orientation are important factors in determining the affinity of compounds for activated or resting platelet receptors

Cited by 2 publications

References 23 publications

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Covalent chloramine inhibitors of blood platelet functions: Computational indices for their reactivity and antiplatelet activity

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