Download PDF
Synthesis 2017; 49(09): 2025-2034
DOI: 10.1055/s-0036-1588692
paper
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Anti-Stereoselective Ring-Opening Reactions of Azabicyclic Alkenes with Fluoroalkylamines

Wen Yang
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China   Email: yangdq@scnu.edu.cn
,
Guo Cheng
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China   Email: yangdq@scnu.edu.cn
,
Yue Li
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China   Email: yangdq@scnu.edu.cn
,
Xiongjun Zuo
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China   Email: yangdq@scnu.edu.cn
,
Dingqiao Yang*
Guangzhou Key Laboratory of Materials for Energy Conversion and Storage, School of Chemistry and Environment, South China Normal University, Guangzhou 510006, P. R. China   Email: yangdq@scnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 11 November 2016

Accepted after revision: 15 December 2016

Publication Date:
13 January 2017 (online)

    Permissions and Reprints All articles of this category


Abstract

A novel iridium-catalyzed ring-opening reaction of azabicyclic alkenes with a variety of fluoroalkylamines was developed. The reaction gave a series of fluorinated trans-1,2-diamine derivatives in good to excellent yields (up to 98%) under relatively mild conditions. The effects of various ligands, catalyst loading, solvents, and temperatures on the yield of the reaction were also investigated. This is the first time that fluorinated compounds were synthesized by incorporating a series of fluoroalkylamines into hydronaphthalene skeleton.

Key words

iridium catalyst - fluoroalkylamines - azabicyclic alkenes - ring-opening reaction - fluorinated trans-1,2-diamines

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588692. Copies of 1H, 13C{1H} and 19F NMR spectra for compounds 3aa–af, 3aj–ak, 3ba–bb, 3bd–be, 3bk, 3ca–cb, 3cd–ce, 3da–db, 3dd–de, 3dk, 3ea–eb, and 3ed–ee, as well as the HPLC conditions and spectra of compound 3aa, are included.
  • Supporting Information
 

  • References


      • For reviews, see:
    • 1a Ward RS. Chem. Soc. Rev. 1990; 19: 1
      Crossref
    • 1b Lautens M. Synthesis 1993; 177
    • 1c Lautens M, Fagnou K, Hiebert S. Acc. Chem. Res. 2003; 36: 48
      CrossrefPubMed
    • 1d Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
      CrossrefPubMed
    • 1e Fagnou K, Lautens M. Chem. Rev. 2003; 103: 169
      CrossrefPubMed
    • 1f Rayabarapu DK, Cheng C.-H. Acc. Chem. Res. 2007; 40: 971
      CrossrefPubMed
    • 1g Drusan M, Šebesta R. Tetrahedron 2014; 70: 759
      Crossref
    • 1h Yang D.-Q, Han Y.-F. Chin. J. Org. Chem. 2006; 26: 1613
    • 1i Cheng H.-C, Liang X.-L, Li X.-L, Long Y.-H, Yang D.-Q. Chin. J. Org. Chem. 2012; 32: 433
      Crossref
    • 1j Wu R.-H, Yang W, Cheng G, Li Y, Yang D.-Q. Chin. J. Org. Chem. 2016; 36: 2368
      Crossref

      For reviews, see:
    • 2a Costello GF, James R, Shaw JS, Slater AM, Stutchbury NC. J. Med. Chem. 1991; 34: 181
      CrossrefPubMed
    • 2b Snyder SE, Aviles-Garay FA, Chakraborti R, Nichols DE, Watts VJ, Mailman RB. J. Med. Chem. 1995; 38: 2395
      CrossrefPubMed
    • 2c Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V, Fiorentini F, Olgiati V, Ghiglieri A, Govoni S. J. Med. Chem. 1995; 38: 942
      CrossrefPubMed
    • 2d Kim K, Guo Y, Sulikowski GA. J. Org. Chem. 1995; 60: 6866
      Crossref
  • 3 Nakamura M, Matsuo K, Inoue T, Nakamura E. Org. Lett. 2003; 5: 1373
    CrossrefPubMed
    • 4a Lautens M, Rovis T. J. Am. Chem. Soc. 1997; 119: 11090
    • 4b Ma S.-H, Lautens M. J. Org. Chem. 1996; 61: 7246
      CrossrefPubMed
    • 4c Rayabarapu DK, Chiou C.-F, Cheng C.-H. Org. Lett. 2002; 4: 1679
      CrossrefPubMed
    • 4d Zeng Z.-Y, Yang D.-Q, Long Y.-H, Pan X.-J, Huang G.-B, Zuo X.-J, Zhou W. J. Org. Chem. 2014; 79: 5249
      CrossrefPubMed
    • 4e Feng C.-C, Nandi M, Sambaiah T, Cheng C.-H. J. Org. Chem. 1999; 64: 3538
      CrossrefPubMed
    • 5a Bos PH, Rudolph A, Pérez M, Martín FM, Harutyunyan SR, Feringa BL. Chem. Commun. 2012; 48: 1748
      CrossrefPubMed
    • 5b Millet R, Bernardez T, Palais L, Alexakis A. Tetrahedron Lett. 2009; 50: 3474
      Crossref
    • 5c Bertozzi F, Pineschi M, Macchia F, Arnold LA, Minnaard AJ, Feringa BL. Org. Lett. 2002; 4: 2703
      CrossrefPubMed
    • 5d Arrayas RG, Cabrera S, Carretero JC. Org. Lett. 2005; 7: 219
      CrossrefPubMed
    • 5e Pineschi M, Del Moro F, Crotti P, Macchia F. Org. Lett. 2005; 7: 3605
      CrossrefPubMed
  • 6 Millward DB, Sammis G, Waymouth RM. J. Org. Chem. 2000; 65: 3902
    CrossrefPubMed
    • 7a Villeneuve K, Tam W. J. Am. Chem. Soc. 2006; 128: 3514
      CrossrefPubMed
    • 7b Burton RR, Tam W. Org. Lett. 2007; 9: 3287
      CrossrefPubMed
    • 7c Tenaglia A, Marc S. J. Org. Chem. 2008; 73: 1397
      CrossrefPubMed
    • 7d Ballantine M, Menard ML, Tam W. J. Org. Chem. 2009; 74: 7570
      CrossrefPubMed
    • 7e Tenaglia A, Marc S, Giordano L, De Riggi I. Angew. Chem. Int. Ed. 2011; 50: 9062
      CrossrefPubMed
    • 8a Lautens M, Fagnou K, Yang D.-Q. J. Am. Chem. Soc. 2003; 125: 14884
      CrossrefPubMed
    • 8b Cho Y.-H, Zunic V, Senboku H, Olsen M, Lautens M. J. Am. Chem. Soc. 2006; 128: 6837
      CrossrefPubMed
    • 8c Zhang L, Le CM, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 5951
      CrossrefPubMed
    • 8d Loh CC. J, Fang X, Peters B, Lautens M. Chem. Eur. J. 2015; 21: 13883
      CrossrefPubMed
    • 8e Loh CC, Schmid M, Peters B, Fang X, Lautens M. Angew. Chem. Int. Ed. 2016; 55: 4600
      Crossref
    • 8f Zhu J.-T, Tsui GC, Lautens M. Angew. Chem. Int. Ed. 2012; 51: 12353
      CrossrefPubMed
    • 9a Li L.-P, Rayabarapu DK, Nandi M, Cheng C.-H. Org. Lett. 2003; 5: 1621
      CrossrefPubMed
    • 9b Fan B.-M, Li S.-F, Chen H.-L, Lu Z.-W, Liu S.-S, Yang Q.-G, Yu L, Xu J.-B, Zhou Y.-Y, Wang J. Adv. Synth. Catal. 2013; 355: 2827
      Crossref
    • 9c McManus HA, Fleming MJ, Lautens M. Angew. Chem. Int. Ed. 2007; 46: 433
      CrossrefPubMed
    • 9d Lu Z.-W, Wang J, Han B.-Q, Li S.-F, Zhou Y.-Y, Fan B.-M. Adv. Synth. Catal. 2015; 357: 3121
      Crossref
    • 9e Li Y, Yang W, Cheng G, Yang D.-Q. J. Org. Chem. 2016; 81: 4744
      CrossrefPubMed
    • 10a Yang D.-Q, Long Y.-H, Wang H, Zhang Z.-M. Org. Lett. 2008; 10: 4723
      CrossrefPubMed
    • 10b Long Y.-H, Yang D.-Q, Zhang Z.-M, Wu Y.-J, Zeng H.-P, Chen Y. J. Org. Chem. 2010; 75: 7291
      CrossrefPubMed
    • 10c Cheng H.-C, Yang D.-Q. J. Org. Chem. 2012; 77: 9756
      Crossref
    • 10d Luo R.-S, Liao J.-H, Tang W.-J, Chan AS. C. Chem. Commun. 2013; 49: 9959
      Crossref
    • 10e Zeng C.-Y, Yang F, Chen J.-C, Wang J, Fan B.-M. Org. Biomol. Chem. 2015; 13: 8425
      Crossref
    • 10f Yang W, Luo R.-S, Yang D.-Q. Molecules 2015; 20: 21103
      CrossrefPubMed
    • 11a Pan X.-J, Huang G.-B, Long Y.-H, Zuo X.-J, Xu X, Gu F.-L, Yang D.-Q. J. Org. Chem. 2014; 79: 187
      CrossrefPubMed
    • 11b Meng L, Yang W, Pan X.-J, Tao M, Cheng G, Wang S.-Y, Zeng H.-P, Long Y.-H, Yang D.-Q. J. Org. Chem. 2015; 80: 2503
      CrossrefPubMed
  • 12 Sawama Y, Kawamoto K, Satake H, Krause N, Kita Y. Synlett 2010; 2151
    Article in Thieme Connect
  • 13 Lautens M, Fagnou K, Taylor M, Rovis T. J. Organomet. Chem. 2001; 624: 259
    Crossref
  • 14 Leong P, Lautens M. J. Org. Chem. 2004; 69: 2194
    CrossrefPubMed
  • 15 Yang D.-Q, Xia J.-Y, Long Y.-H, Zeng Z.-Y, Zuo X.-J, Wang S.-Y, Li C.-R. Org. Biomol. Chem. 2013; 11: 4871
    CrossrefPubMed
  • 16 Lautens M, Dockendorff C, Fagnou K, Malicki A. Org. Lett. 2002; 4: 1311
    CrossrefPubMed
  • 17 Nishimura T, Tsurumaki E, Kawamoto T, Guo X.-X, Hayashi T. Org. Lett. 2008; 10: 4057
    CrossrefPubMed
  • 18 Henderson JL, Buchwald SL. Org. Lett. 2010; 12: 4442
    CrossrefPubMed
  • 19 Brusoe AT, Hartwig JF. J. Am. Chem. Soc. 2015; 137: 8460
    CrossrefPubMed
    • 20a Arlow SI, Hartwig JF. Angew. Chem. Int. Ed. 2016; 55: 4567
      CrossrefPubMed
    • 20b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
      CrossrefPubMed
    • 20c Hagmann WK. J. Med. Chem. 2008; 51: 4359
      CrossrefPubMed
    • 20d Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
      CrossrefPubMed
    • 20e Smart BE. J. Fluorine Chem. 2001; 109: 3
      Crossref
    • 21a Lautens M, Fagnou K, Zunic V. Org. Lett. 2002; 4: 3465
      CrossrefPubMed
    • 21b Lautens M, Dockendorff C. Org. Lett. 2003; 20: 3695
    • 21c Allen A, Marquand PL, Burton R, Villeneuve K, Tam W. J. Org. Chem. 2007; 72: 7849
      CrossrefPubMed