Document Type: Short communication

Author

Faculty of Science and Engineering, Macquarie University, North Ryde, NSW 2109, Australia

Abstract

Hybridization, functionalization, and enantioseparation of ethano-bridged Tröger base analogs have been performed. X-ray crystallographic analysis, chiral HPLC and CD spectroscopy have assigned the absolute configuration of the obtained ethano-bridged Tröger base analogs, confirming their optical purity. These optically active building blocks are readily modifiable and owing to their versatility they offer unique benefits for the growing community of molecular machinists.

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[1] Stoddart J.F. Angew. Chem. Int. Ed., 2017, 56:11094

[2] Sluysmans D.,  Stoddart J.F. Proc. Natl. Acad. Sci. U.S.A., 2018, 115:9359

[3] Kazem-Rostami M., Akhmedov N.G., Faramarzi S. J. Mol. Struct., 2019, 1178:538

[4] Dolenský B., Elguero J., Král V., Pardo C., Valík M., Current Tröger's Base Chemistry. In Adv. Heterocycl. Chem.; Academic Press: United States, 2007; p 56

[5] Bandara H.M.D., Burdette S.C. Chem. Soc. Rev., 2012, 41:1809

[6] Kazem-Rostami M. Synthesis, 2017, 49:1214

[7] Cowart M.D., Sucholeiki I., Bukownik R.R., Wilcox C.S. J. Am. Chem. Soc., 1988, 110:6204

[8] Cai K., Lipke M.C., Liu Z., Nelson J., Cheng T., Shi Y., Cheng C., Shen D., Han J.-M., Vemuri S., Feng Y., Stern C.L., Goddard W.A., Wasielewski M.R.,  Stoddart J.F. Nat. Commun., 2018, 9:5275

[9] Kiehne U., Weilandt T., Lützen A. Eur. J. Org. Chem., 2008, 2008:2056

[10] Kiehne U., Weilandt T., Lützen A. Org. Lett., 2007, 9:1283

[11] Bhaskar Reddy M., Shailaja M., Manjula A., Premkumar J.R., Sastry G.N., Sirisha K., Sarma A.V.S. Org. Biomol. Chem., 2015, 13:1141

[12] Boyle E.M., Comby S., Molloy J.K., Gunnlaugsson T. J. Org. Chem., 2013, 78:8312

[13] Kazem-Rostami M. Synlett, 2017, 28:1641

[14] Kazem-Rostami M., Moghanian A. Org. Chem. Front., 2017, 4:224

[15] Kazem-Rostami M. New J. Chem., 2019, 43:7751

[16] Hamada Y., Mukai S. Tetrahedron Asymmetry, 1996, 7:2671

[17] Michon C., Sharma A., Bernardinelli G., Francotte E.  Lacour J. Chem. Commun., 2010, 46:2206

[18] Kamiyama T., Sigrist L.,Cvengroš J. Synthesis, 2016, 48:3957

[19] Sharma A., Besnard C., Guenee L. Lacour J. Org. Biomol. Chem., 2012, 10:966

[20] Sharma A., Guenee L., Naubron J.-V. Lacour J. Angew. Chem., Int. Ed., 2011, 50:3677

[21] Bosmani A., Guarnieri-Ibáñez A. Lacour J. Helv. Chim. Acta, 2019, 102:1900021

[22] Alessandro B., Alejandro G.I., Sébastien G., Céline B. Jérôme L. Angew. Chem. Int. Ed., 2018, 57:7151

[23] Michon C., Gonçalves-Farbos M.-H. Lacour J. Chirality, 2009, 21:809

[24] Weatherly C.A., Na Y.-C., Nanayakkara Y.S., Woods R.M., Sharma A., Lacour J., Armstrong D.W. J. Chromatogr. B, 2014, 955:72

[25] Satishkumar S., Periasamy M. Tetrahedron Asymmetry, 2006, 17:1116

[26] Didier D., Tylleman B., Lambert N., Vande Velde C.M.L., Blockhuys F., Collas A., Sergeyev S. Tetrahedron, 2008, 64:6252

[27] Jameson D.L., Field T., Schmidt M.R., DeStefano A.K., Stiteler C.J., Venditto V.J., Krovic B., Hoffman C.M., Ondisco M.T., Belowich M.E. J. Org. Chem., 2013, 78:11590

[28] Didier D., Sergeyev S. Eur. J. Org. Chem., 2007, 2007:3905

[29] Jensen J., Tejler J., Wärnmark K. J. Org. Chem., 2002, 67:6008

[30] Jarzebski A., Bannwarth C., Tenten C., Benkhaeuser C., Schnakenburg G., Grimme S. Lützen A. Synthesis, 2015, 47:3118

[31] Bishop R.R. J. Appl. Chem., 1956, 6:256

[32] Kiehne U., Lützen A. Synthesis, 2004, 2004:1687

[33] Tatar A., Valík M., Novotná J., Havlík M., Dolenský B., Král V., Urbanová M. Chirality, 2014, 26:361

[34] Malik Q.M., Ijaz S., Craig D.C., Try A.C. Tetrahedron, 2011, 67:5798

[35] Artacho J., Wärnmark K. Synthesis, 2009, 2009:3120

[36] Dusso D., Ramirez C., Parise A., Lanza P., Vera D.M., Chesta C., Moyano E.L., Akhmedov N.G. Magn. Reson. Chem., 2019, 57:423

[37] Didier D., Sergeyev S. Tetrahedron, 2007, 63:3864

[38] Benkhäuser-Schunk C., Wezisla B., Urbahn K., Kiehne U.,  Daniels J.,  Schnakenburg G., Neese F., Lützen A. ChemPlusChem, 2012, 77:396

[39] Weilandt T., Kiehne U., Bunzen J., Schnakenburg G., Lützen A. Chem. Eur. J., 2010, 16:2418

[40] Kiehne U., Bruhn T., Schnakenburg G., Fröhlich R., Bringmann G., Lützen A. Chem. Eur. J., 2008, 14:4246

[41] Ishida Y., Ito H., Mori D., Saigo K. Tetrahedron Lett., 2005, 46:109

[42] Faroughi M., Zhu K.-X., Jensen P., Craig D.C., Try A.C. Eur. J. Org. Chem., 2009, 2009:4266

[43] Pereira R., Pfeifer L., Fournier J., Gouverneur V., Cvengroš J. Org. Biomol. Chem., 2017, 15:628

[44] Sergeyev S., Didier D., Boitsov V., Teshome A., Asselberghs I., Clays K., Vande Velde C.M.L., Plaquet A., Champagne B. Chem. Eur. J., 2010, 16:8181

[45] Kazem-Rostami M. J. Therm. Anal. Calorim., 2019,

[46] Maugeri L., Lébl T., Cordes D.B., Slawin A.M.Z., Philp D. J. Org. Chem., 2017, 82:1986

[47] Maugeri L., Jamieson E.M.G., Cordes D.B., Slawin A.M.Z., Philp D. Chem. Sci., 2017, 8:938

[48] Maugeri L., Asencio-Hernández J., Lébl T., Cordes D.B., Slawin A.M.Z.,  Delsuc M.-A., Philp D. Chem. Sci., 2016, 7:6422

[49] Banerjee S., Bright S.A., Smith J.A., Burgeat J., Martinez-Calvo M., Williams D.C., Kelly J.M., Gunnlaugsson T. J. Org. Chem., 2014, 79:9272