2019
DOI: 10.3762/bjoc.15.33
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Synthesis of C3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step

Abstract: We demonstrate a new synthetic strategy toward star-shaped C 3-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting from readily available 4’-iodoacetophenone and L-serine. These C 3-symmetric molecules containing AAA moieties are useful to design new ligands suitable for asymmetric synthesis and peptide dendrimers.

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Cited by 7 publications
(6 citation statements)
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“…For example, 200 was synthesized via direct introduction of a (S)-alanine unit by Negishi reaction (Scheme 27). 61,62 Although many syntheses of C 2 -symmetric bis-amino acid derivatives have been reported using chiral auxiliary as described in section 2.3, there are no reports, to our knowledge, of their use in the synthesis of C 3 -symmetric tris-amino acid derivatives. On the other hand, asymmetric hydrogenation has been used in the synthesis of C 3 -symmetric tris-amino acid derivatives: Frejd et al synthesized compounds 203a and 203b with three dehydroamino acid units at positions 1,3,5 by the HWE reaction of 1,3,5-triformylbenzene and the Mizorogi-Heck reaction of 1,3,5-triiodobenzene, respectively (Scheme 28).…”
Section: Reviewmentioning
confidence: 99%
“…For example, 200 was synthesized via direct introduction of a (S)-alanine unit by Negishi reaction (Scheme 27). 61,62 Although many syntheses of C 2 -symmetric bis-amino acid derivatives have been reported using chiral auxiliary as described in section 2.3, there are no reports, to our knowledge, of their use in the synthesis of C 3 -symmetric tris-amino acid derivatives. On the other hand, asymmetric hydrogenation has been used in the synthesis of C 3 -symmetric tris-amino acid derivatives: Frejd et al synthesized compounds 203a and 203b with three dehydroamino acid units at positions 1,3,5 by the HWE reaction of 1,3,5-triformylbenzene and the Mizorogi-Heck reaction of 1,3,5-triiodobenzene, respectively (Scheme 28).…”
Section: Reviewmentioning
confidence: 99%
“…The resultant trimerized synthon was then used in a Negishi cross-coupling with palladium as a catalyst in DMF at 80 °C, yielding a compound with a 68% yield ( Table 2 , entry 7). 1 …”
Section: Functionalized Side Armsmentioning
confidence: 99%
“…In particular, C3-symmetric geometries are present in star-shaped molecules, dendrimers, molecular cages, metal-organic frameworks (MOFs), and covalent organic frameworks (COFs). [1][2][3][4][5] C3-symmetric conjugated aromatic compounds have applications ranging from optoelectronic and self-assembling systems to liquid crystals, mesogens, and nonlinear material optics. [6][7][8] Notably, C3-symmetric molecules have good physicochemical characteristics, making them useful as active building blocks in electronic devices, including organic eld-effect transistors (OFETs), organic photovoltaic devices (OPVs), organic solar cells (OSCs), and organic light-emitting diodes (OLEDs).…”
Section: Introductionmentioning
confidence: 99%
“…We also employed palladium-catalyzed Negishi and Heck cross-coupling reactions to assemble starshaped molecules. [38] For example, to assemble tris-AAA derivative 161 and peptide derivatives 162-164,w eu sed Negishi cross-coupling reactions as a key step (Scheme 49). First, triiodo derivative 7 was prepared by the trimerizationo f4 -iodoacetophenone (37).…”
Section: Negishi Cross-coupling Reactionsmentioning
confidence: 99%