Synthesis 2019; 51(10): 2081-2099
DOI: 10.1055/s-0037-1612420
short review
© Georg Thieme Verlag Stuttgart · New York

Different Strategies for Obtaining Enantiopure Hemicryptophanes

Cédric Colomban
,
Bastien Châtelet
,
Alexandre Martinez*
This research was supported by Agence National de la Recherche (ANR, France, OH Risque grant ANR-14-OHRI-0015-03).
Further Information

Publication History

Received: 06 December 2018

Accepted after revision: 13 February 2019

Publication Date:
24 April 2019 (online)


Abstract

Hemicryptophanes have recently emerged as an attractive class of cages due to their interesting applications as supramolecular receptors and catalysts. Over the last decade, substantial advances have been made regarding the preparation of enantiopure versions of these synthetic receptors. Enantiopure hemicryptophanes are commonly obtained through the separation of diastereomers by chromatography, or by resolution of racemic mixtures using chiral HPLC. This short review summarizes the existing methods to access to these chiral organic architectures and discusses the benefits and drawbacks of each approach.

1 Introduction

2 Enantiopure Hemicryptophanes Obtained by Introducing Additional Chiral Units and Separation of Diastereomers

2.1 Synthesis by Means of Intramolecular Macrocyclization Reactions

2.2 [1+1] Coupling of the CTV and the Southern Part

3 Enantiopure Hemicryptophanes Obtained by Means of Chiral HPLC Resolution of Enantiomers

3.1 Resolution of Hemicryptophane Racemates

3.2 Resolution of CTV-Based Precursor Racemates

4 Conclusion

 
  • References

    • 2a Chen LJ, Yang HB, Shionoya M. Chem. Soc. Rev. 2017; 46: 2555
    • 2b Beuerle F, Bappaditya G. Angew. Chem. Int. Ed. 2018; 57: 4850
  • 3 Saalfrank RW, Scheurer A. Top. Curr. Chem. 2012; 319: 125
  • 4 Jędrzejewska H, Szumna A. Chem. Rev. 2017; 117: 4863
  • 5 Zhang D, Ronson TK, Nitschke JR. Acc. Chem. Res. 2018; 51: 2423
  • 6 Brown CJ, Toste FD, Bergman RG, Raymond KN. Chem. Rev. 2015; 115: 3012
  • 7 Ousaka N, Grunder S, Castilla AM, Whalley AC, Stoddart JF, Nitschke JR. J. Am. Chem. Soc. 2012; 134: 15528
  • 8 Henkelis JJ, Carruthers CJ, Chambers SE, Clowes R, Cooper AI, Fisher J, Hardie MJ. J. Am. Chem. Soc. 2014; 136: 14393
  • 9 Schaly A, Rousselin Y, Chambron J.-C, Aubert E, Espinosa E. Eur. J. Inorg. Chem. 2016; 832
    • 10a Wierzbicki M, Jędrzejewska H, Szumna A. Chiral Calixarenes. In Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier; Waltham (MA, USA): 2014
    • 10b Iwamoto K, Shimizu H, Shinkai S. J. Am. Chem. Soc. 1993; 115: 3997
    • 10c Karpus A, Yesypenko O, Boiko V, Daran J.-C, Voitenko Z, Kalchenko V, Manoury E. J. Org. Chem. 2018; 83: 1146
    • 10d Tlustý M, Slavík P, Kohout M, Eigner V, Lhoták P. Org. Lett. 2017; 19: 2933
    • 10e Talotta C, Gaeta C, Troisi F, Monaco G, Zanasi R, Mazzeo G, Rosini C, Neri P. Org. Lett. 2010; 12: 2912
    • 10f Slavik P, Kohout M, Bohm S, Eigner V, Lhotak P. Chem. Commun. 2016; 52: 2366
    • 10g Aragay GG, Ballester P. Chem. Sci. 2016; 7: 5976
    • 11a Szumna A. Chem. Soc. Rev. 2010; 39: 4274
    • 11b Cram DJ, Karbach S, Kim HE, Knobler CB, Maverick EF, Ericson JL, Helgeson RC. J. Am. Chem. Soc. 1988; 110: 2229
    • 11c Moran JR, Karbach S, Cram DJ. J. Am. Chem. Soc. 1982; 104: 5826
    • 11d Soncini P, Bonsignore S, Dalcanale E, Ugozzoli F. J. Org. Chem. 1992; 57: 4608
    • 11e Beyeh NK, Fehér D, Luostarinen M, Schalley CA, Rissanen K. J. Inclusion Phenom. Macrocyclic Chem. 2006; 56: 381
    • 11f Shivanyuk A, Rissanen K, Körner SK, Rudkevich DM, Rebek JJr. Helv. Chim. Acta 2000; 83: 1778
    • 11g Vachon J, Harthong S, Dubessy B, Dutasta J.-P, Vanthuyne N, Roussel C, Naubron J.-V. Tetrahedron: Asymmetry 2010; 21: 1534
    • 11h Vachon J, Harthong S, Jeanneau E, Aronica C, Vanthuyne N, Roussel C, Dutasta J.-P. Org. Biomol. Chem. 2011; 9: 5086
    • 11i Concilio G, Talotta C, Gaeta C, Neri P, Monaco G, Zanasi R, Tedesco D, Bertucci C. J. Org. Chem. 2017; 82: 202
    • 11j Iwanek W, Stefańska K, Szumna A, Wierzbicki M. RSC Adv. 2016; 6: 13027
    • 11k Grajda M, Wierzbicki M, Cmoch P, Szumna A. J. Org. Chem. 2013; 78: 11597
    • 11l Wierzbicki M, Głowacka AA, Szymański MP, Szumna A. Chem. Commun. 2017; 53: 5200
  • 12 Kobayashi K, Yamanaka M. Chem. Soc. Rev. 2015; 44: 449
    • 13a Huc I. Eur. J. Org. Chem. 2004; 1: 17
    • 13b Ferrand Y, Kendhale AM, Kauffmann B, Grélard A, Marie C, Blot V, Pipelier M, Dubreuil D, Huc I. J. Am. Chem. Soc. 2010; 132: 7858
    • 13c Ferrand Y, Chandramouli N, Kendhale AM, Aube C, Kauffmann B, Grélard A, Laguerre M, Dubreuil D, Huc I. J. Am. Chem. Soc. 2012; 134: 11282
    • 13d Tsiamantas C, de Hatten X, Douat C, Kauffmann B, Maurizot V, Ihara H, Takafuji M, Metzler-Nolte N, Huc I. Angew. Chem. Int. Ed. 2016; 55: 6848
    • 13e Chandramouli N, Ferrand Y, Lautrette G, Kauffmann B, Mackereth CD, Laguerre M, Dubreuil D, Huc I. Nat. Chem. 2015; 7: 334
    • 14a Brotin T, Dutasta J.-P. Chem. Rev. 2009; 109: 88
    • 14b El-Ayle G, Holman KT. Cryptophanes . In Comprehensive Supramolecular Chemistry II . Atwood JL, Gokel GW, Barbour LJ. Elsevier; New York: 2017
    • 14c Jenkelis JJ, Hardie MJ. Chem. Commun. 2015; 51: 11929
    • 14d Oldknow S, Martir DR, Pritchard VE, Blitz MA, Fishwick CW. G, Zysman-Colman E, Hardie MJ. Chem. Sci. 2018; 9: 8150
    • 14e Kai S, Kojima T, Thorp-Greenwood FL, Hardie MJ, Hiraoka S. Chem. Sci. 2018; 9: 4104
    • 14f Brégier F, Hudeček O, Chaux F, Penouilh M.-J, Chambron J.-C, Lhoták P, Aubert E, Espinosa E. Eur. J. Org. Chem. 2017; 3795
    • 14g Joseph AI, Lapidus SH, Kane CM, Holman KT. Angew. Chem. Int. Ed. 2015; 54: 1471
    • 14h Rose HM, Witte C, Rossella F, Klippel S, Freund C, Schröder L. Proc. Natl. Acad. Sci. U.S.A. 2014; 111: 11697
    • 14i Kotera N, Tassali N, Léonce E, Boutin C, Berthault P, Brotin T, Dutasta J.-P, Delacour L, Traoré T, Buisson D.-A, Taran F, Coudert S, Rousseau B. Angew. Chem. Int. Ed. 2012; 51: 4100
    • 14j Riggle BA, Wang Y, Dmochowski IJ. J. Am. Chem. Soc. 2015; 137: 5542
    • 14k Brotin T, Jeanneau E, Berthault P, Léonce E, Pitrat D, Mulatier J.-C. J. Org. Chem. 2018; 83: 14465
    • 14l Chapellet L.-L, Cochrane JR, Mari E, Boutin C, Berthault P, Brotin T. J. Org. Chem. 2015; 80: 6143
    • 15a Crini G. Chem. Rev. 2014; 114: 10940
    • 15b Engeldinger E, Armspach D, Matt D. Chem. Rev. 2003; 103: 4147
    • 15c Gingter S, Bezdushna E, Ritter H. Beilstein J. Org. Chem. 2011; 7: 204
    • 15d Gramage-Doria R, Armspach S, Matt D. Coord. Chem. Rev. 2013; 257: 776
    • 15e Pedersen CM, Bols M. Cyclodextrin-Based Artificial Enzymes: Synthesis and Function. In Organic Synthesis and Molecular Engineering. Nielsen MB. John Wiley & Sons; Hoboken: 2014. 305
    • 15f Marinescu L, Bols M. Curr. Org. Chem. 2010; 14: 1380
    • 15g Jouffroy M, Gramage-Doria R, Sémeril D, Armspach D, Matt D, Oberhauser W, Toupet L. Beilstein J. Org. Chem. 2014; 10: 2388
    • 15h Jouffroy M, Armspach D, Matt D. Dalton Trans. 2015; 44: 12942
    • 15i Jouffroy M, Gramage-Doria R, Armspach D, Sémeril D, Oberhauser W, Matt D, Toupet L. Angew. Chem. Int. Ed. 2014; 53: 3937
    • 15j Guitet M, Zhang P, Marcelo F, Tugny C, Jiménez-Barbero J, Buriez O, Amatore C, Mouriès-Mansuy V, Goddard J.-P, Fensterbank J, Zhang Y, Roland S, Ménand M, Sollogoub M. Angew. Chem. Int. Ed. 2013; 52: 7213
    • 15k Zhang P, Tugny C, Meijide Suárez J, Guitet M, Derat E, Vanthuyne N, Zhang Y, Bistri O, Mouriès-Mansuy V, Ménand M, Roland S, Fensterbank L, Sollogoub M. Chem 2017; 3: 174
    • 15l Zhang P, Meijide Suárez J, Driant T, Derat E, Zhang Y, Ménand M, Roland S, Sollogoub M. Angew. Chem. Int. Ed. 2017; 56: 10821
    • 16a Zhiquan L, Polen S, Hadad CM, RajanBabu TV, Badjić JD. J. Am. Chem. Soc. 2016; 138: 8253
    • 16b Chen S, Yamasaki M, Shane P, Gallucci J, Hadad CM, Badjić JD. J. Am. Chem. Soc. 2015; 137: 12276
    • 16c Chen S, Ruan Y, Brown JD, Hadad CM, Badjić JD. J. Am. Chem. Soc. 2014; 136: 1733
    • 16d Chen S, Ruan Y, Brown JD, Gallucci J, Maslak V, Hadad CM, Badjić JD. J. Am. Chem. Soc. 2013; 135: 14964
    • 16e Zhiquan L, Xie H, Border SE, Gallucci J, Pavlović RZ, Badjić JD. J. Am. Chem. Soc. 2018; 140: 11091
  • 17 Dalla Cort A, Mandolini L, Pasquini C, Schiaffino L. New J. Chem. 2004; 28: 1198
    • 18a Canceill J, Collet A, Gabard J, Kotzyba-Hibert F, Lehn J.-M. Helv. Chim. Acta 1982; 65: 1894
    • 18b Zhang D, Martinez A, Dutasta J.-P. Chem. Rev. 2017; 117: 4900
    • 19a Hardie MJ. Chem. Soc. Rev. 2010; 39: 516
    • 19b Canceill J, Collet A, Gabard J, Gottarelli G, Spada GP. J. Am. Chem. Soc. 1985; 107: 1299
  • 20 Gautier A, Mulatier J.-C, Crassous J, Dutasta J.-P. Org. Lett. 2005; 7: 1207
  • 21 Perraud O, Martinez A, Dutasta J.-P. Chem. Commun. 2011; 47: 5861
  • 22 Schmitt A, Perraud O, Payet E, Chatelet B, Bousquet B, Valls M, Padula D, Di Bari L, Dutasta J.-P, Martinez A. Org. Biomol. Chem. 2014; 12: 4211
  • 23 Zhang D, Mulatier J.-C, Cochrane JR, Guy L, Gao G, Dutasta J.-P, Martinez A. Chem. Eur. J. 2016; 22: 8038
  • 24 Lefevre S, Simonet R, Pitrat D, Mulatier J.-C, Vanthuyne N, Jean M, Dutasta J.-P, Guy L, Martinez A. ChemistrySelect 2016; 1: 6316
  • 25 Cochrane JR, Schmitt A, Wille U, Hutton CA. Chem. Commun. 2013; 49: 8504
  • 26 Brégier F, Karuppannan S, Chambron J.-C. Eur. J. Org. Chem. 2012; 10: 1920
  • 27 Chatelet B, Joucla L, Padula D, Bari LD, Pilet G, Robert V, Dufaud V, Dutasta J.-P, Martinez A. Org. Lett. 2015; 17: 500
  • 28 Brégier F, Lavalle J, Chambron J.-C. Eur. J. Org. Chem. 2013; 13: 2666
  • 29 Perraud O, Dimitrov Raytchev P, Martinez A, Dutasta J.-P. Chirality 2010; 22: 885
  • 30 Dimitrov Raytchev P, Martinez A, Gornitzka H, Dutasta JP. J. Am. Chem. Soc. 2011; 133: 2157
  • 31 Payet E, Dimitrov-Raytchev P, Chatelet B, Guy L, Grass S, Lacour J, Dutasta JP, Martinez A. Chirality 2012; 24: 1077
  • 32 Zhang D, Bousquet B, Mulatier JC, Pitrat D, Jean M, Vanthuyne N, Guy L, Dutasta JP, Martinez A. J. Org. Chem. 2017; 82: 6082
  • 33 Canceill J, Collet A, Gottarelli G, Palmeri P. J. Am. Chem. Soc. 1987; 109: 6454
  • 34 Long A, Perraud O, Albalat M, Robert V, Dutasta J.-P, Martinez A. J. Org. Chem. 2018; 83: 6301
  • 35 Chatelet B, Payet E, Perraud O, Dimitrov-Raytchev P, Chapellet L.-L, Dufaud V, Martinez A, Dutasta J.-P. Org. Lett. 2011; 13: 3706
  • 36 Lefevre S, Zhang D, Godart E, Jean M, Vanthuyne N, Mulatier JC, Dutasta JP, Guy L, Martinez A. Chem. Eur. J. 2016; 22: 2068
  • 37 Zhang D, Jamieson K, Guy L, Gao G, Dutasta JP, Martinez A. Chem. Sci. 2017; 8: 789
  • 38 Zhang D, Dutasta JP, Dufaud V, Guy L, Martinez A. ACS Catal. 2017; 7: 7340
  • 39 Lefevre S, Héloin A, Pitrat D, Mulatier JC, Vanthuyne N, Jean M, Dutasta JP, Guy L, Martinez A. J. Org. Chem. 2016; 81: 3199
  • 40 Kraszewska A, Rivera-Fuentes P, Rapenne G, Crassous J, Petrovic AG, Alonso-Gómez JL, Huerta E, Diederich F, Thilgen C. Eur. J. Org. Chem. 2010; 4402