3117-83-7Relevant academic research and scientific papers
Synthesis of isocyanides by reacting primary amines with difluorocarbene
Si, Yi-Xin,Zhu, Peng-Fei,Zhang, Song-Lin
supporting information, p. 9086 - 9090 (2020/11/30)
A general, convenient, and friendly route for preparing a versatile building block of isocyanides from primary amines is developed. Difluorocarbene, generated in situ from decarboxylation of chlorodifluoroacetate, reacts efficiently with primary amines to produce isocyanides. Various primary amines are well tolerated, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is demonstrated, showing its practical capacity in drug design and peptide modification.
One-step synthesis of natural product-inspired biaryl ether-cyclopeptoid macrocycles by double ugi multiple-component reactions of bifunctional building blocks
Michalik, Dirk,Schaks, Angela,Wessjohann, Ludger A.
, p. 149 - 157 (2007/10/03)
Isonitrile-functionalized biaryl ethers can serve as key building blocks for the highly efficient one-step production of natural product inspired-macrocycles, with six or even twelve new bonds and rings with up to 50 members being formed in total yields o
Synthesis of steroid-biaryl ether hybrid macrocycles with high skeletal and side chain variability by multiple multicomponent macrocyclization including bifunctional building blocks
Wessjohann, Ludger A.,Rivera, Daniel G.,Coll, Francisco
, p. 7521 - 7526 (2007/10/03)
(Chemical Equation Presented) Utilizing the multiple multicomponent macrocyclization including bifunctional building blocks (MiB) strategy, a library of nonracemic, nonrepetitive peptoid-containing steroid - biaryl ether hybrid macrocycles was built. Up to 16 new bonds, including those of the macrocyclization, can be formed in one pot simultaneously while introducing varied elements of diversity. Functional diversity is generated primarily by choosing Ugi-reactive functional building blocks, bearing the respective recognition or catalytic motifs. These appear attached to the peptoid backbone of the macrocyclic cavity, similar to side chains of amino acids found in enzyme active sites. Likewise, skeletal diversity is based on the variation of defined bifunctional building blocks which allow the parallel formation of macrocyclic cavities that are highly diverse in shape and size and thus perspectively in function. This straightforward approach is suitable to generate multifunctional macrocycles for applications in catalysis, supramolecular, or biological chemistry.
Supramolecular compounds from multiple ugi multicomponent macrocyclizations: Peptoid-based cryptands, cages, and cryptophanes
Rivera, Daniel G.,Wessjohann, Ludger A.
, p. 7122 - 7123 (2007/10/03)
The first 3-fold multicomponent macrocyclizations of trifunctional building blocks were developed to produce, in one pot, cryptands, cages, and cryptophanes with peptoid tethers carrying additional recognition motifs. The straightforward, efficient, and d
