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Collect. Czech. Chem. Commun. 1979, 44, 2653-2659
https://doi.org/10.1135/cccc19792653

Synthesis and chiroptical properties of (-)-(1R)-3-azatricyclo[5,4,0,04,9]undecan-2-one - A lactam with non-planar cis-amide group

Miloš Tichý, Petr Maloň, Ivo Frič and Karel Bláha

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6

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  • Pazderková Markéta, Profant Václav, Seidlerová Beata, Dlouhá Helena, Hodačová Jana, Jávorfi Tamás, Siligardi Giuliano, Baumruk Vladimír, Bednárová Lucie, Maloň Petr: Electronic Circular Dichroism of the Chiral Rigid Tricyclic Dilactam with Nonplanar Tertiary Amide Groups. J. Phys. Chem. B 2014, 118, 11100. <https://doi.org/10.1021/jp5063463>
  • Pazderková Markéta, Profant Václav, Hodačová Jana, Šebestík Jaroslav, Pazderka Tomáš, Novotná Pavlína, Urbanová Marie, Šafařík Martin, Buděšínský Miloš, Tichý Miloš, Bednárová Lucie, Baumruk Vladimír, Maloň Petr: Nonplanar Tertiary Amides in Rigid Chiral Tricyclic Dilactams. Peptide Group Distortions and Vibrational Optical Activity. J. Phys. Chem. B 2013, 117, 9626. <https://doi.org/10.1021/jp405226k>
  • Bednárová Lucie, Maloň Petr, Bouř Petr: Spectroscopic properties of the nonplanar amide group: A computational study. Chirality 2007, 19, 775. <https://doi.org/10.1002/chir.20462>
  • Woody Robert W.: A simple model for the optical properties of chiral amides. Biopolymers 1983, 22, 189. <https://doi.org/10.1002/bip.360220128>
  • Krow Grant R.: Nitrogen insertion reactions of bridged bicyclic ketones. Regioselective lactam formation. Tetrahedron 1981, 37, 1283. <https://doi.org/10.1016/S0040-4020(01)92445-7>
  • TICHY M., MALON P., FRIC I., BLAHA K.: ChemInform Abstract: SYNTHESIS AND CHIROPTICAL PROPERTIES OF (‐)‐(1R)‐3‐AZATRICYCLO(5.4.0.04,9)UNDECAN‐2‐ONE, A LACTAM WITH A NON‐PLANAR CIS‐AMIDE GROUP. Chemischer Informationsdienst 1979, 10. <https://doi.org/10.1002/chin.197952231>