Synthesis 2017; 49(10): 2117-2128
DOI: 10.1055/s-0036-1588765
short review
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Syntheses of Isoxazolidin-5-ones

Julien Annibaletto
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France   Email: jean-francois.briere@insa-rouen.fr
,
Sylvain Oudeyer
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France   Email: jean-francois.briere@insa-rouen.fr
,
Vincent Levacher
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France   Email: jean-francois.briere@insa-rouen.fr
,
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France   Email: jean-francois.briere@insa-rouen.fr
› Author Affiliations
Further Information

Publication History

Received: 07 February 2017

Accepted after revision: 02 March 2017

Publication Date:
04 April 2017 (online)


Abstract

This short review provides an overview concerning the developments toward the catalytic enantioselective syntheses of isoxazolidin-5-one derivatives making use of metal-based or organocatalytic conditions. The subsequent use and chemical transformations of these valuable chiral oxazole heterocycles will also be described.

1 Introduction

2 Aza-Michael Strategy

3 Nitroso-Based Annulation Strategy

4 Nitrone-Based Annulation Strategy

5 Functionalization Reactions of Isoxazolidin-5-ones

6 Miscellaneous

7 Conclusion

 
  • References

  • 1 Cabrele C. Reiser O. J. Org. Chem. 2016; 81: 10109
    • 2a Lovering F. Bikker J. Humblet C. J. Med. Chem. 2009; 52: 6752
    • 2b Lovering F. Med. Chem. Commun. 2013; 4: 515
    • 3a Janecki T. Wąsek T. Różalski M. Krajewska U. Studzian K. Janecka A. Bioorg. Med. Chem. Lett. 2006; 16: 1430
    • 3b Shamsuzzaman, Khanam H. Mashrai A. Siddiqui N. Tetrahedron Lett. 2013; 54: 874

      For representative examples, see:
    • 4a Xiang Y. Gi H.-J. Niu D. Schinazi RF. Zhao K. J. Org. Chem. 1997; 62: 7430
    • 4b Merino P. Franco S. Garces N. Merchan FL. Tejero T. Chem. Commun. 1998; 493
    • 4c Merino P. Franco S. Merchan FL. Tejero T. J. Org. Chem. 2000; 65: 5575
    • 4d Merino P. del Alamo EM. Bona M. Franco S. Merchan FL. Tejero T. Vieceli O. Tetrahedron Lett. 2000; 41: 9239
    • 4e Romeo G. Chiacchio U. Corsaro A. Merino P. Chem. Rev. 2010; 110: 3337
  • 5 Berthet M. Cheviet T. Dujardin G. Parrot I. Martinez J. Chem. Rev. 2016; 116: 15235
    • 6a Baldwin JE. Harwood LM. Lombard MJ. Tetrahedron 1984; 40: 4363
    • 6b Pearson C. Rinehart KL. Sugano M. Costerison JR. Org. Lett. 2000; 2: 2901
    • 6c Lee H.-S. Park J.-S. Kim BM. Gellman SH. J. Org. Chem. 2003; 68: 1575
    • 6d Shindo M. Ohtsuki K. Shishido K. Tetrahedron: Asymmetry 2005; 16: 2821
    • 6e Bentley SA. Davies SG. Lee JA. Roberts PM. Russell AJ. Thomson JE. Toms SM. Tetrahedron 2010; 66: 4604
    • 7a Enantioselective Synthesis of β-Amino Acids . 2nd ed.; Juaristi E. Soloshonok VA. John Wiley & Sons; Hoboken: 2005
    • 7b Aguilar M.-I. Purcell AW. Devi R. Lew R. Rossjohn J. Smith AI. Perlmutter P. Org. Biomol. Chem. 2007; 5: 2884
    • 7c Seebach D. Gardiner J. Acc. Chem. Res. 2008; 41: 1366
    • 7d Kim SM. Yang JW. Org. Biomol. Chem. 2013; 11: 4737
    • 7e Cabrele C. Martinek TA. Reiser O. Berlicki Ł. J. Med. Chem. 2014; 57: 9718
  • 8 Juarez-Garcia ME. Yu S. Bode JW. Tetrahedron 2010; 66: 4841

    • For selected representative examples, see:
    • 9a Freer A. Overton K. Tomanek R. Tetrahedron Lett. 1990; 31: 1471
    • 9b Ishikawa T. Nagai K. Kudoh T. Saito S. Synlett 1995; 1171
    • 9c Jost S. Gimbert Y. Greene AE. Fotiadu F. J. Org. Chem. 1997; 62: 6672
    • 9d Ishikawa T. Nagai K. Kudoh T. Saito S. Synlett 1998; 1291
    • 9e Ben Ayed K. Beauchard A. Poisson J.-F. Py S. Laurent MY. Martel A. Ammar H. Abid S. Dujardin G. Eur. J. Org. Chem. 2014; 2924
  • 10 Sibi MP. Liu M. Org. Lett. 2000; 2: 3393
  • 11 Niu D. Zhao K. J. Am. Chem. Soc. 1999; 121: 2456
  • 12 Sibi MP. Prabagaran N. Ghorpade SG. Jasperse CP. J. Am. Chem. Soc. 2003; 125: 11796
  • 13 Sibi MP. Liu M. Org. Lett. 2001; 3: 4181
    • 14a Ibrahem I. Rios R. Vesely J. Zhao G.-L. Córdova A. Chem. Commun. 2007; 849
    • 14b Ibrahem I. Rios R. Vesely J. Zhao G.-L. Córdova A. Synthesis 2008; 1153
    • 15a Pou A. Moyano A. Eur. J. Org. Chem. 2013; 3103
    • 15b Yousfi T. Elliott A. Hanane M. Merdes R. Moyano A. Molecules 2016; 21: 1655
  • 16 Berini C. Sebban M. Oulyadi H. Sanselme M. Levacher V. Brière J.-F. Org. Lett. 2015; 17: 5408
    • 17a For reviews on Meldrum’s acid in catalysis, see: Dumas AM. Fillion E. Acc. Chem. Res. 2010; 43: 440
    • 17b Pair E. Cadart T. Levacher V. Brière J.-F. ChemCatChem 2016; 8: 1882
  • 18 Izumi S. Kobayashi Y. Takemoto Y. Org. Lett. 2016; 18: 696
  • 19 Zuman P. Shah B. Chem. Rev. 1994; 94: 1621
  • 20 Seayad J. Patra PK. Zhang Y. Ying JY. Org. Lett. 2008; 10: 953
  • 21 Glorius F. Altenhoff G. Goddard R. Lehmann C. Chem. Commun. 2002; 2704
  • 22 Nawaz F. Zaghouani M. Bonne D. Chuzel O. Rodriguez J. Coquerel Y. Eur. J. Org. Chem. 2013; 8253
  • 23 Ji S.-P. Liu L.-W. Chen F. Ren H.-X. Yang Y. Zhang Z.-B. Peng L. Wang L.-X. Eur. J. Org. Chem. 2016; 5437
  • 24 Postikova S. Tite T. Levacher V. Brière J.-F. Adv. Synth. Catal. 2013; 355: 2513
  • 25 Guinchard X. Vallée Y. Denis J.-N. Org. Lett. 2005; 7: 5147
  • 26 Tite T. Sabbah M. Levacher V. Brière J.-F. Chem. Commun. 2013; 49: 11569
  • 27 Cadart T. Berthonneau C. Levacher V. Perrio S. Brière J.-F. Chem. Eur. J. 2016; 43: 15261
  • 28 Seebach D. Beck AK. Capone S. Deniau G. Grošelj U. Zass E. Synthesis 2009; 1
    • 29a Avenoza A. Busto JH. Corzana F. Jimenez-Oses G. Peregrina JM. Chem. Commun. 2004; 980
    • 29b Avenoza A. Busto JH. Jiménez-Osés G. Peregrina JM. Org. Lett. 2006; 8: 2855
    • 29c García-González I. Mata L. Corzana F. Jiménez-Osés G. Avenoza A. Busto JH. Peregrina JM. Chem. Eur. J. 2015; 21: 1156
  • 30 For a review on PTC, see: Shirakawa S. Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
  • 31 Brière J.-F. Oudeyer S. Dalla V. Levacher V. Chem. Soc. Rev. 2012; 41: 1696

    • For reviews on the catalytic formation of sulfanylated compounds bearing a quaternary center, see:
    • 32a Clayden J. MacLellan P. Beilstein J. Org. Chem. 2011; 7: 582
    • 32b Chauhan P. Mahajan S. Enders D. Chem. Rev. 2014; 114: 8807
    • 32c Yu J.-S. Huang H.-M. Ding P.-G. Hu X.-S. Zhou F. Zhou J. ACS Catal. 2016; 6: 5319
  • 33 Zhang H. Zhang S.-J. Zhou Q.-Q. Dong L. Chen Y.-C. Beilstein J. Org. Chem. 2012; 8: 1241