Synlett 2015; 26(10): 1283-1288
DOI: 10.1055/s-0034-1380412
synpacts
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in the Synthesis of 2-Substituted Oxetanes

Owen A. Davis
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK   Email: j.bull@imperial.ac.uk
,
James A. Bull*
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK   Email: j.bull@imperial.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 22 January 2015

Accepted after revision: 12 February 2015

Publication Date:
16 March 2015 (online)


Abstract

Recent interest in oxetanes in medicinal chemistry and as synthetic intermediates has led to the development of a number of methods for the synthesis of more functionalized and highly substituted oxetane derivatives. Here we review cyclization approaches for the preparation of 2-substituted oxetanes. Methods involving C–O bond formation, as well as recently developed C–C bond forming cyclization strategies are highlighted.

 
  • References

    • 1a Ghosh B, Urban MW. Science 2009; 323: 1458
    • 1b Shibutani R, Tsutsumi H. J. Power Sources 2012; 202: 369
    • 1c Schulte B, Dannenberg CA, Keul H, Möller M. J. Polym. Sci., Part A: Polym. Chem. 2013; 51: 1243

      For selected recent examples, see:
    • 2a Gronnier C, Kramer S, Odabachian Y, Gagosz F. J. Am. Chem. Soc. 2012; 134: 828
    • 2b Ruider SA, Müller S, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 11908
  • 3 Wang Z, Chen Z, Sun J. Org. Biomol. Chem. 2014; 12: 6028
  • 4 Burkhard JA, Wuitschik G, Rogers-Evans M, Müller K, Carreira EM. Angew. Chem. Int. Ed. 2010; 49: 9052
    • 5a Wuitschik G, Rogers-Evans M, Müller K, Fischer H, Wagner B, Schuler F, Polonchuk L, Carreira EM. Angew. Chem. Int. Ed. 2006; 45: 7736
    • 5b Wuitschik G, Carreira EM, Wagner B, Fischer H, Parrilla I, Schuler F, Rogers-Evans M, Müller K. J. Med. Chem. 2010; 53: 3227
    • 6a For paclitaxel, see: Wani MC, Taylor HL, Wall ME. J. Am. Chem. Soc. 1971; 93: 2325
    • 6b For Oxetin (glutamine antimetabolite), see: Ōmura S, Murata M, Imamura N, Iwai Y, Tanaka H. J. Antibiot. 1984; 37: 1324
  • 7 For a recent study on oxetane metabolic stability, see: Stepan AF, Karki K, McDonald WS, Dorff PH, Dutra JK, DiRico KJ, Won A, Subramanyam C, Efremov IV, O’Donnell CJ, Nolan CE, Becker SL, Pustilnik LR, Sneed B, Sun H, Lu Y, Robshaw AE, Riddell D, O’Sullivan TJ, Sibley E, Capetta S, Atchison K, Hallgren AJ, Miller E, Wood A, Obach RS. J. Med. Chem. 2011; 54: 7772
    • 8a Duncton MA. J, Estiarte MA, Johnson RJ, Cox M, O’Mahony DJ. R, Edwards WT, Kelly MG. J. Org. Chem. 2009; 74: 6354
    • 8b Duncton MA. J, Estiarte MA, Tan D, Kaub C, O’Mahony DJ. R, Johnson RJ, Cox M, Edwards WT, Wan M, Kincaid J, Kelly MG. Org. Lett. 2008; 10: 3259
  • 9 Carreira EM, Fessard TC. Chem. Rev. 2014; 114: 8257
    • 10a Du J, Chun B.-K, Mosley RT, Bansal S, Bao H, Espiritu C, Lam AM, Murakami E, Niu C, Micolochick Steuer HM, Furman PA, Sofia MJ. J. Med. Chem. 2014; 57: 1826
    • 10b Jonckers TH. M, Vandyck K, Vandekerckhove L, Hu L, Tahri A, Van Hoof S, Lin T.-I, Vijgen L, Berke JM, Lachau-Durand S, Stoops B, Leclercq L, Fanning G, Samuelsson B, Nilsson M, Rosenquist Å, Simmen K, Raboisson P. J. Med. Chem. 2014; 57: 1836
  • 11 Wuitschik G, Rogers-Evans M, Buckl A, Bernasconi M, Märki M, Godel T, Fischer H, Wagner B, Parrilla I, Schuler F, Schneider J, Alker A, Schweizer WB, Müller K, Carreira EM. Angew. Chem. Int. Ed. 2008; 47: 4512
  • 12 Burkhard JA, Guérot C, Knust H, Carreira EM. Org. Lett. 2012; 14: 66
    • 13a Okuma K, Tanaka Y, Kaji S, Ohta H. J. Org. Chem. 1983; 48: 5133
    • 13b Butova ED, Barabash AV, Petrova AA, Kleiner CM, Schreiner PR, Fokin AA. J. Org. Chem. 2010; 75: 6229
  • 14 Sone T, Lu G, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2009; 48: 1677
    • 15a Abe M. J. Chin. Chem. Soc. 2008; 55: 479
    • 15b D’Auria M, Racioppi R. Molecules 2013; 18: 11384
  • 17 Griesbeck AG, Franke M, Neudörfl J, Kotaka H. Beilstein J. Org. Chem. 2011; 7: 127
  • 18 Morgan KF, Hollingsworth IA, Bull JA. Chem. Commun. 2014; 50: 5203

    • For other studies on deprotonation of oxetanes and trapping with electrophiles, see:
    • 19a Coppi DI, Salomone A, Perna FM, Capriati V. Chem. Commun. 2011; 47: 9918
    • 19b Geden JV, Beasley BO, Clarkson GJ, Shipman M. J. Org. Chem. 2013; 78: 12243
  • 20 Davis OA, Bull JA. Angew. Chem. Int. Ed. 2014; 53: 14230

    • For enantioenriched bromohydrins, see:
    • 21a Wei S, Messerer R, Tsogoeva SB. Chem. Eur. J. 2011; 17: 14380
    • 21b Ren J, Dong W, Yu B, Wu Q, Zhu D. Tetrahedron: Asymmetry 2012; 23: 497
    • 21c Zhou Y, Gao G, Song Y, Qu J. Synth. Commun. 2014; 44: 1515