Download PDF
Synthesis 2019; 51(10): 2107-2115
DOI: 10.1055/s-0037-1612217
feature
© Georg Thieme Verlag Stuttgart · New York

Silanediol Anion Binding and Enantioselective Catalysis

Jonathan W. Attard
a   Worcester Polytechnic Institute, Department of Chemistry and Biochemistry, Worcester, MA 01609, USA   Email: aemattson@wpi.edu
,
Kohei Osawa
b   Yamagata University, Department of Biochemical Engineering, Graduate School of Science and Engineering, Yonezawa, Yamagata 992-8510, Japan
,
Yong Guan
a   Worcester Polytechnic Institute, Department of Chemistry and Biochemistry, Worcester, MA 01609, USA   Email: aemattson@wpi.edu
,
Jessica Hatt
a   Worcester Polytechnic Institute, Department of Chemistry and Biochemistry, Worcester, MA 01609, USA   Email: aemattson@wpi.edu
,
Shin-ichi Kondo
b   Yamagata University, Department of Biochemical Engineering, Graduate School of Science and Engineering, Yonezawa, Yamagata 992-8510, Japan
,
Anita Mattson*
a   Worcester Polytechnic Institute, Department of Chemistry and Biochemistry, Worcester, MA 01609, USA   Email: aemattson@wpi.edu
› Author AffiliationsThe National Science Foundation (1362030), the National Institutes of Health (1R35GM12480401), and Worcester Polytechnic Institute (WPI) are gratefully acknowledged for providing support for our studies. K.O. was supported by a fellowship from Yamagata University to study in the Mattson laboratory to complete these investigations. J.W.A. was supported by a WPI global scholars fellowship to complete investigations in the Kondo laboratory. J.H. is grateful for a WPI Summer Undergraduate Research Fellowship that supported her contribution to this project.
Further Information

Publication History

Received: 11 January 2019

Accepted after revision: 14 January 2019

Publication Date:
12 March 2019 (online)

    Permissions and Reprints All articles of this category


Abstract

Silanediols possess unique and complementary catalytic activity in reactions that are likely to proceed through anion binding. This article directly compares silanediols, thioureas, and squaramides in three separate anion-binding processes. The catalytic abilities of select members of each family are directly correlated to association constants.

Key words

anion recognition - enantioselective catalysis - thiourea - silanediol - squaramide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612217.
  • Supporting Information
 

  • References


      • For recent reviews on silanediols, see:
    • 1a Wieting JM, Hardman-Baldwin AM, Visco MD, Mattson AE. Aldrichimica Acta 2016; 49: 15
    • 1b Franz AK, Wilson SO. J. Med. Chem. 2013; 56: 388
      CrossrefPubMed
    • 1c Sieburth SM, Chen C.-A. Eur. J. Org. Chem. 2006; 311
    • 1d Min GK, Heranandez D, Skryidstrup T. Acc. Chem. Res. 2013; 46: 457
      CrossrefPubMed
  • 2 Kondo S, Harada T, Tanaka R, Unno M. Org. Lett. 2006; 8: 4621
    CrossrefPubMed
  • 3 For a recent example of silanediols involved in sensing, see: Kondo S, Hie Y, Yamaura M. Org. Lett. 2013; 15: 520
    CrossrefPubMed

      • For selected examples of silanediols involved in achiral catalysis, see:
    • 4a Tran NT, Min T, Franz AK. Chem. Eur. J. 2011; 17: 9897
      CrossrefPubMed
    • 4b Schafer AG, Wieting JM, Mattson AE. Org. Lett. 2011; 13: 5228
      CrossrefPubMed
    • 4c Hardman-Baldwin AM, Mattson AE. ChemSusChem 2014; 7: 3275
      CrossrefPubMed

      For reviews on anion-binding catalysis, see:
    • 5a Visco MD, Attard J, Guan Y, Mattson AE. Tetrahedron Lett. 2017; 58: 2623
      Crossref
    • 5b Busschaert N, Caltagirone C, Van Rossom W, Gale PA. Chem. Rev. 2015; 115: 8038
      CrossrefPubMed
    • 5c Brak K, Jacobsen EN. Angew. Chem. Int. Ed. 2013; 52: 534
      CrossrefPubMed

      For examples of silanediols plausibly involved in enantioselective anion-binding catalysis, see:
    • 6a Guan Y, Attard JW, Visco MD, Fisher TJ, Mattson AE. Chem. Eur. J. 2018; 24: 7123
      CrossrefPubMed
    • 6b Hardman-Baldwin AM, Visco MD, Wieting JM, Stern C, Kondo S, Mattson AE. Org. Lett. 2016; 18: 2883
      CrossrefPubMed
    • 6c Wieting JM, Fisher TJ, Schafer AG, Visco MD, Galluci JC, Mattson AE. Eur. J. Org. Chem. 2015; 525
    • 6d Schafer AG, Wieting JM, Fisher TJ, Mattson AE. Angew. Chem. Int. Ed. 2013; 52: 11321
      CrossrefPubMed

      For select examples of processes plausibly proceeding through thiourea anion binding catalysis, see:
    • 7a Park Y, Harper KC, Kuhl N, Kwan EE, Liu RY, Jacobsen EN. Science 2017; 355: 162
      CrossrefPubMed
    • 7b Jarvis CL, Hirschi JS, Vetticatt MJ, Seidel D. Angew. Chem. Int. Ed. 2017; 56: 2670
      CrossrefPubMed
    • 7c Kennedy CR, Kehnerr D, Rajapaksa NS, Ford DD, Park Y, Jacobsen EN. J. Am. Chem. Soc. 2016; 138: 13525
      CrossrefPubMed
    • 7d Zhao C, Chen SB, Seidel D. J. Am. Chem. Soc. 2016; 138: 9053
      CrossrefPubMed
    • 7e Reisman SE, Doyle AG, Jacobsen EN. J. Am. Chem. Soc. 2008; 130: 7198
      CrossrefPubMed
    • 7f De CK, Clauber EG, Seidel D. J. Am. Chem. Soc. 2009; 131: 17060
      CrossrefPubMed
    • 7g Taylor MS, Tokunaga N, Jacobsen EN. Angew. Chem. Int. Ed. 2005; 44: 6700
      CrossrefPubMed

      For examples of plausible enantioselective squaramide anion binding catalysis, see:
    • 8a Wendlandt AE, Vangal P, Jacobsen EN. Nature 2018; 556: 447
    • 8b Banik SM, Levina A, Hyde AM, Jacobsen EN. Science 2017; 358: 761
      PubMed
    • 8c Liu RY, Wasa M, Jacobsen EN. Tetrahedron Lett. 2015; 56: 3428
      CrossrefPubMed
  • 9 Kotke M, Schreiner PR. Tetrahedron 2006; 62: 434
    Crossref
  • 10 Raheem IT, Thiara PV, Peterson EA, Jacobsen EN. J. Am. Chem. Soc. 2007; 129: 13404
    CrossrefPubMed
    • 11a Fischer T, Bamberger J, Gomez-Martinez M, Piekarski DG, Mancheno O. Angew. Chem. Int. Ed. 2018; 57 DOI: in press; 10.1002/anie.201812031.
      Crossref
    • 11b Fischer T, Duang Q.-N, Mancheno OG. Chem. Eur. J. 2017; 23: 5983
      CrossrefPubMed
    • 11c Mancheno OG, Asmus S, Zurro M, Fischer T. Angew. Chem. Int. Ed. 2015; 54: 8823
      CrossrefPubMed
    • 11d Zurro M, Asmus S, Beckendorf S, Muck-Lichtenfeld C, Mancheno OG. J. Am. Chem. Soc. 2014; 136: 13999
      CrossrefPubMed
    • 11e Ohmatus K, Kiyokawa M, Ooi T. J. Am. Chem. Soc. 2011; 133: 1307
      CrossrefPubMed
    • 11f Ohmatsu J, Ando Y, Ooi T. J. Am. Chem. Soc. 2013; 135: 18706
      CrossrefPubMed

      For reviews including naturally occurring bioactive chromanones and tetrahydroxanthones, see:
    • 12a Masters KS, Brase S. Chem. Rev. 2012; 112: 3717
      CrossrefPubMed
    • 12b Wezeman T, Brase S, Masters KS. Nat. Prod. Rep. 2015; 32: 6
      CrossrefPubMed
  • 13 Thiourea 11 and squaramide 12 were employed in these studies so that a stronger UV/Vis response may be observed.
  • 14 Knowles RR, Lin S, Jacobsen EN. J. Am. Chem. Soc. 2010; 132: 5030
    CrossrefPubMed
  • 15 Corrected for 5:1 silanediol:Et2O content.