Enantioselective approach to indolizidine and quinolizidine scaffolds. Application to the synthesis of peptide mimics

Lu, Yuanyuan; Alujas-Burgos, Sílvia; Oliveras-González, Cristina; Vázquez-Jiménez, Laura; Rojo, Pep; Álvarez‐Larena, Ángel; Bayón, Pau; Figueredo, Marta

doi:10.1016/j.tet.2017.11.042

Cited by 6 publications

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References 47 publications

(19 reference statements)

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“…N -Heterocycles are among the most significant structural components of pharmaceuticals, and more than half of the FDA approved small-molecule drugs contain at least one N -heterocyclic ring . Quinolizidines, as one family of N -heterocycles, are extremely important components of modern pharmaceuticals and serve as versatile building blocks in organic synthesis . Meanwhile, quinolizidine derivatives are also the indispensable frameworks of numerous natural products, as shown in Figure .…”

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Synthesis of 1-Amino-2H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

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2019

Org. Lett.

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An efficient tandem cycloisomerization–amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.

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confidence: 99%

Synthesis of 1-Amino-2H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis

Min

Sun

2019

Org. Lett.

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Enantioselective Palladium‐Catalyzed N‐Allylation of Lactams

et al. 2018

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N-Deprotonated five-, six-, seven, and nine-membered lactams undergo smooth palladium-catalyzed N-allylation with methyl-(pent-3-en-2-yl)-carbonate or 2-chloro-3-pentene. With axially chiral bisphosphane ligands, enantioselectivities ranging from 83 to 97% ee are reached. The configuration of one of the allylation products is assigned unambiguously by the preparation of a relay compound and by analogy to the others. Using the enantioselective allylation protocol as a key step, dvalerolactam is converted into (4S,9aR)-4-methylquinolizidine.

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