Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part III

Andreas Jarzebski; Christoph Bannwarth; Christina Tenten; Christian Benkhäuser; Gregor Schnakenburg; Stefan Grimme; Arne Lützen

doi:10.1055/s-0035-1560181

Synthesis, Table of Contents

Synthesis 2015; 47(20): 3118-3132
DOI: 10.1055/s-0035-1560181

feature

Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part III

Authors

Andreas Jarzebski

^aKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Email: arne.luetzen@uni-bonn.de
Christoph Bannwarth

^bMulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4, 53115 Bonn, Germany
Christina Tenten

^aKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Email: arne.luetzen@uni-bonn.de
Christian Benkhäuser

^aKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Email: arne.luetzen@uni-bonn.de
Gregor Schnakenburg

^cInstitut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Stefan Grimme

^bMulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4, 53115 Bonn, Germany
Arne Lützen*

^aKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Email: arne.luetzen@uni-bonn.de

Abstract

All articles of this category

Abstract

Eleven different derivatives of Tröger’s base were synthesized and successfully resolved by (recycling) HPLC on chiral stationary (S,S)-Whelk-O1 or CHIRALPAK IA phase on a (semi-) preparative scale or synthesized in enantiomerically pure form. The absolute configuration was determined by X-ray crystal structure analysis, comparison of the quantum chemically calculated circular dichroism spectra with the experimental spectra, or comparison of specific rotations with literature data.

Key words

Tröger’s base - enantiomeric resolution - HPLC techniques - circular dichroism - time-dependent density functional theory

Full Text

References

References
1 New address: C. Benkhäuser, Knauer Wissenschaftliche Geräte GmbH, Hegauer Weg 38, 14163 Berlin, Germany.
2 Tröger J. J. Prakt. Chem. 1887; 36: 225
3 Spielman MA. J. Am. Chem. Soc. 1935; 57: 583
4 Larson SB, Wilcox CS. Acta Crystallogr. Ser. C 1986; 42: 224
5 Prelog V, Wieland P. Helv. Chim. Acta 1944; 27: 1127
6 Wilen SH, Qi JZ, Williard PG. J. Org. Chem. 1991; 56: 485

7a Webb TH, Wilcox CS. Chem. Soc. Rev. 1993; 22: 383
7b Valík M, Strongin RM, Král V. Supramol. Chem. 2005; 17: 347
7c Dolenský B, Elguero J, Král V, Pardo C, Valík M. Adv. Heterocycl. Chem. 2007; 93: 1
7d Sergeyev S. Helv. Chim. Acta 2009; 92: 415
7e Dolenský B, Havlík M, Král V. Chem. Soc. Rev. 2012; 41: 3839
7f Rúnarsson ÖV, Artacho J, Wärnmark K. Eur. J. Org. Chem. 2012; 7015

Recent examples not covered by the reviews in ref. 7:

8a Boyle EM, Comby S, Molloy JK, Gunnlaugsson T. J. Org. Chem. 2013; 78: 8312
8b Gardarsson H, Schweizer WB, Trapp N, Diederich F. Chem. Eur. J. 2014; 20: 4608
8c Tatar A, Valík M, Novotné J, Havlík M, Dolenský B, Král V, Urbanová M. Chirality 2014; 26: 361
8d Banerjee S, Bright SA, Smith JA, Burgeat J, Martinez-Calvo M, Williams DC, Kelly JM, Gunnlaugsson T. J. Org. Chem. 2014; 79: 9272
8e Reddy MR, Shailaja M, Manjula A, Premkumar JR, Sastry GN, Sirisha K, Sarma AV. S. Org. Biomol. Chem. 2015; 13: 1141

Recent examples not covered by the reviews in ref. 7:

9a Elmes RB, Erby M, Bright SA, Williams DC, Gunnlaugsson T. Chem. Commun. 2012; 48: 2588
9b Manda BR, Alla M, Ganji RJ, Addlagatta A. Eur. J. Med. Chem. 2014; 86: 39

Recent examples not covered by the reviews in ref. 7:

10a Pereira R, Cvengroš J. J. Organomet. Chem. 2013; 729: 81
10b Pereira R, Cvengroš J. Eur. J. Org. Chem. 2013; 4233

Recent examples not covered by the reviews in ref. 6:

11a Ramírez CL, Procaccini R, Chesta CA, Parise AR, Vera DM. A. Org. Electron. 2013; 14: 2564
11b Neogi I, Ghosh A, Chow TJ, Moorthy JN. Org. Electron. 2014; 15: 3766
11c Neogi I, Jhulki S, Ghosh A, Chow TJ, Moorthy JN. ACS Appl. Mater. Interfaces 2015; 7: 3298

Recent examples not covered by the reviews in ref. 7:

12a Wang Z, Wang D, Zhang F, Jin J. ACS Macro Lett. 2014; 3: 597
12b Carta M, Croad M, Malpass-Evans R, Jansen JC, Bernardo P, Clarizia G, Friess K, Lanč M, McKeown NB. Adv. Mater. 2014; 26: 3526
12c Zhuang Y, Seong JG, Do YS, Jo HJ, Cui Z, Lee J, Lee YM, Guiver MD. Macromolecules 2014; 41: 3254
12d Tocci E, De Lorenzo L, Bernardo P, Clarizia G, Bazzarelli F, McKeown NB, Carta M, Malpass-Evans R, Friess K, Pilnáček K, Lanč M, Yampolskii YP, Strarannikova L, Shantarovich V, Mauri M, Jansen JC. Macromolecules 2014; 47: 7900
12e Carta M, Malpass-Evans R, Croad M, Rogan Y, Lee M, Rose I, McKeown NB. Polym. Chem. 2014; 5: 5267
12f Zhou J, Zhu X, Hu J, Liu H, Hu Y, Jiang J. Phys. Chem. Chem. Phys. 2014; 16: 6075
12g Madrid E, Rong Y, Carta M, McKeown NB, Malpass-Evans R, Attard GA, Clarke TJ, Taylor SH, Long Y.-T, Marken F. Angew. Chem. Int. Ed. 2014; 53: 10751
12h Yang Z.-Z, Zhang H, Yu B, Zhao Y, Ji G, Liu Z. Chem. Commun. 2015; 51: 1271

13a Jensen J, Wärnmark K. Synthesis 2001; 1873
13b Hansson A, Jensen J, Wärnmark K. Eur. J. Org. Chem. 2003; 3179

14a Jensen J, Strozyk M, Wärnmark K. Synthesis 2002; 2761
14b Kiehne U, Lützen A. Synthesis 2004; 1687
14c Hof F, Schar M, Scofield DM, Fischer F, Diederich F, Sergeyev S. Helv. Chim. Acta 2005; 88: 2333
14d Solano C, Svensson D, Olomi Z, Jensen J, Wendt OF, Wärnmark K. Eur. J. Org. 2005; 3510
14e Bew SP, Legentil L, Scholier V, Sharma SV. Chem. Commun. 2007; 389
14f Didier D, Sergeyev S. Tetrahedron 2007; 63: 3864

15a Lützen A, Hapke M, Griep-Raming J, Haase D, Saak W. Angew. Chem. Int. Ed. 2002; 41: 2086
15b Bunzen J, Bruhn T, Bringmann G, Lützen A. J. Am. Chem. Soc. 2009; 131: 3621
15c Bunzen J, Hovorka R, Lützen A. J. Org. Chem. 2009; 74: 5228
15d Bunzen J, Hapke M, Lützen A. Eur. J. Org. Chem. 2009; 3885
15e Gütz C, Hovorka R, Schnakenburg G, Lützen A. Chem. Eur. J. 2013; 19: 10890
15f Gütz C, Hovorka R, Stobe C, Struch N, Topić F, Schnakenburg G, Rissanen K, Lützen A. Eur. J. Org. Chem. 2014; 206
15g Gütz C, Hovorka R, Klein C, Jiang Q.-Q, Bannwarth C, Engeser M, Schmuck C, Assenmacher W, Mader W, Topić F, Rissanen K, Grimme S, Lützen A. Angew. Chem. Int. Ed. 2014; 53: 1693
15h Klein C, Gütz C, Bogner M, Topić F, Rissanen K, Lützen A. Angew. Chem. Int. Ed. 2014; 53: 3739
15i Gütz C, Hovorka R, Struch N, Bunzen J, Meyer-Eppler G, Qu Z.-W, Grimme S, Rissanen K, Topić F, Rissanen K, Cetina M, Engeser M, Lützen A. J. Am. Chem. Soc. 2014; 136: 11830

16a Piehler T, Lützen A. Z. Naturforsch. B 2010; 65b: 329
16b Hovorka R, Hytteballe S, Piehler T, Meyer-Eppler G, Topić F, Rissanen K, Engeser M, Lützen A. Beilstein J. Org. Chem. 2014; 10: 432
16c Hovorka R, Piehler T, Meyer-Eppler G, Hytteballe S, Engeser M, Topić F, Rissanen K, Lützen A. Chem. Eur. J. 2014; 20: 13253

17 Kiehne U, Lützen A. Org. Lett. 2007; 9: 5333

18a Kiehne U, Weilandt T, Lützen A. Org. Lett. 2007; 9: 1283
18b Kiehne U, Lützen A. Eur. J. Org. Chem. 2007; 5703
18c Kiehne U, Weilandt T, Lützen A. Eur. J. Org. Chem. 2008; 2056
18d Weilandt T, Kiehne U, Schnakenburg G, Lützen A. Chem. Commun. 2009; 2320
18e Bunzen J, Kiehne U, Benkhäuser-Schunk C, Lützen A. Org. Lett. 2009; 11: 4786
18f Dalla Favera N, Kiehne U, Bunzen J, Hytteballe S, Lützen A, Piguet C. Angew. Chem. Int. Ed. 2010; 49: 125
18g Weilandt T, Kiehne U, Bunzen J, Schnakenburg G, Lützen A. Chem. Eur. J. 2010; 16: 2418
18h Benkhäuser C, Lützen A. Beilstein J. Org. Chem. 2015; 11: 693

Some recent examples:

19a Shen J, Zhao Y, Inagaki S, Yamamoto C, Shen Y, Liu S, Okamoto Y. J. Chromatogr. A 2013; 1286: 41
19b Hamman C, Wong M, Aliaga I, Ortwine DF, Pease J, Schmidt DE. Jr, Victorino J. J. Chromatogr. A 2013; 1305: 310
19c DaSilva JO, Coes B, Frey L, Mergelsberg I, McClain R, Nogle L, Welch CJ. J. Chromatogr. A 2014; 1328: 98
19d Droux S, Roy M, Félix G. J. Chromatogr. B 2014; 968: 22
19e Wang Z.-Q, Liu J.-D, Chen W, Bai Z.-W. J. Chromatogr. A 2014; 1346: 57
19f Tran LN, Dixit S, Park JH. J. Chromatogr. A 2014; 1356: 289
19g Novell A, Minguillón C. J. Chromatogr. A 2014; 1363: 109
19h Rocchi S, Fanali S, Farkas T, Chankvetadze B. J. Chromatogr. A 2014; 1363: 363
19i Sancho R, Novell A, Svec F, Minguillón C. J. Sep. Sci. 2014; 37: 2805
19j Zhang L, Shen J, Zuo W, Okamoto Y. J. Chromatogr. A 2014; 1365. 86
19k Sciascera L, Ismail O, Ciogli A, Kotoni D, Cavazzini A, Botta L, Szczerba T, Kocergin J, Villani C, Gasparrini F. J. Chromatogr. A 2015; 1383: 160
19l Novell A, Minguillón C. J. Chromatogr. A 2015; 1384: 124

20a Lauber A, Zelenay B, Cvengroš J. Chem. Commun. 2014; 50: 1195
20b Ondrisek P, Schwenk R, Cvengroš J. Chem. Commun. 2014; 50: 9168

21a Tálas E, Margitfalvi J, Machytka D, Czugler M. Tetrahedron: Asymmetry 1998; 9: 4151
21b Miyahara Y, Izumi K, Ibrahim AA, Inazu T. Tetrahedron Lett. 1999; 40: 1705
21c Lenev DA, Lyssenko KA, Golovanov DG, Malyshev OR, Levkin PA, Kostyanovsky RG. Tetrahedron Lett. 2006; 47: 319
21d Sergeyev S, Diederich F. Chirality 2006; 18: 707
21e Řezanka P, Ryšava H, Havlík M, Jakubek M, Sýkora D, Král V. Chirality 2013; 25: 379
21f Řezanka P, Sýkora D, Novotný M, Havlík M, Král V. Chirality 2013; 25: 810
21g Jameson DL, Field T, Schmidt MR, DeStefano AK, Stiteler CJ, Venditto VJ, Krovic B, Hoffman CM, Ondisco MT, Belowich ME. J. Org. Chem. 2013; 78: 11590
21h Suresh S, Periasamy M. Tetrahedron: Asymmetry 2015; 26: 203

22a Kiehne U, Bruhn T, Schnakenburg G, Fröhlich R, Bringmann G, Lützen A. Chem. Eur. J. 2008; 14: 4246
22b Benkhäuser-Schunk C, Wezisla B, Urbahn K, Kiehne U, Daniels J, Schnakenburg G, Neese F, Lützen A. ChemPlusChem 2012; 77: 396
22c Meyer-Eppler G, Vogelsang E, Benkhäuser C, Schnakenburg G, Schneider A, Lützen A. Eur. J. Org. Chem. 2013; 4523
22d Reimers T, Haberhauer G, Benkhäuser C, Schmidtchen FP, Lützen A, Lüning U. Eur. J. Org. Chem. 2013; 7556
22e Meyer-Eppler G, Sure R, Schneider A, Schnakenburg G, Grimme S, Lützen A. J. Org. Chem. 2014; 79: 6679
22f Stobe C, Seto R, Schneider A, Lützen A. Eur. J. Org. Chem. 2014; 6513

23 Please note that the resolution of (rac)-19 could also be achieved recently via diastereomeric salt formation, see ref. 20h. Furthermore, (+)-(5R,11R)-19 and (–)-(5S,11S)-19 could also be prepared in enantiomerically pure form starting from enantiomerically pure disulfoxides, see ref. 19b.
24 Please note that (+)-(5R,11R)-20 could recently be prepared in enantiomerically pure form starting from enantiomerically pure disulfoxides, see ref. 19b.

25a Grimme S. J. Chem. Phys. 2013; 138: 244104
25b Risthaus T, Hansen A, Grimme S. Phys. Chem. Chem. Phys. 2014; 16: 14408
25c Bannwarth C, Grimme S. Comp. Theor. Chem. 2014; 1040-1041: 45
25d Casida ME In Recent Advances in Density Functional Methods . Vol. 1. Chong DP. World Scientific; Singapore: 1995: 155-192

26a Yanai T, Tew DP, Handy NC. Chem. Phys. Lett. 2004; 393: 51
26b Becke AD. Phys. Rev. A 1988; 38: 3098
26c Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785
26d Becke AD. J. Chem. Phys. 1993; 98: 1372

27a Schäfer A, Huber C, Ahlrichs R. J. Chem. Phys. 1994; 100: 5829
27b Weigend F, Ahlrichs R. Phys. Chem. Chem. Phys. 2005; 7: 3297
27c Peterson KA, Figgen D, Goll E, Stoll H, Dolg M. J. Chem. Phys. 2003; 199: 11113

28 Tao J, Perdew JP, Staroverov VN, Scuseria GE. Phys. Rev. Lett. 2003; 91: 146401

29a Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104
29b Grimme S, Ehrlich S, Goerigk L. J. Comp. Chem. 2011; 32: 1456

30a Sheldrick GM. Acta Crystallogr. Ser. A 1990; 46: 467
30b Sheldrick GM. SHELXL-97, Program for Crystal Structure Analysis . University of Göttingen; Germany: 1997
30c Blessing RH. Acta Crystallogr. Ser A. 1995; 51: 33

31 CCDC-1407299 [(+)-(5R,11R)-19], CCDC-1407300 [(–)-(5S,11S)-19], CCDC-1407301 [(+)-(5R,11R)-20], CCDC-1407302 [(–)-(5S,11S)-20], and CCDC-1407303 [(+)-(5R,11R)-23] contain the supplementary data for these structures. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033.

32a Ahlrichs R, Bär M, Häser M, Horn H, Kölmel C. Chem. Phys. Lett. 1989; 162: 165
32b TURBOMOLE, version 6.6, Program Package for ab initio Electronic Structure Calculations. TURBOMOLE GmbH; Karlsruhe, Germany: 2014
32c See also: http://www.turbomole.com.

33 Eichkorn K, Treutler O, Öhm H, Häser M, Ahlrichs R. Chem. Phys. Lett. 1995; 242: 652
34 Weigend F. Phys. Chem. Chem. Phys. 2006; 8: 1057

35a Neese F. ORCA – An ab initio, Density Functional and Semiempirical Program Package, Ver. 3.0. Max Planck Institute for Bioinorganic Chemistry; Germany: 2014
35b Neese F. WIRES Comp. Mol. Sci. 2012; 2: 73

36a Perdew JP, Burke K, Ernzerhof M. Phys. Rev. Lett. 1996; 77: 3865
36b Erratum: Perdew JP, Burke K, Ernzerhof M. Phys. Rev. Lett. 1997; 78: 1396
36c Adamo C, Barone V. J. Chem. Phys. 1999; 110: 6158

Supplementary Material

Supporting Information (PDF) (opens in new window)