Synthesis 2020; 52(06): 853-860
DOI: 10.1055/s-0039-1690763
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Bis-BINOL Derivatives: Linking via the 3-, 4-, or 5-Position by Generation of Suitable C 1-Symmetric Precursors

Martha Kohlhaas
a  Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Fabian Lutz
a  Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Nirtharsan Paransothy
a  Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Frescilia Octa-Smolin
a  Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
,
Christoph Wölper
b  Institute of Inorganic Chemistry, University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany
,
a  Institute of Organic Chemistry and Center for Nanointegration Duisburg-Essen (CENIDE), University of Duisburg-Essen, Universitätsstrasse 7, 45141 Essen, Germany   Email: jochen.niemeyer@uni-due.de
› Author Affiliations
Funding by the Fonds der Chemischen Industrie (Liebig-Fellowship Li 193/02 to J.N.) and Evonik Industries AG (PhD fellowship to M.K.) is gratefully acknowledged.
Further Information

Publication History

Received: 23 October 2019

Accepted after revision: 20 November 2019

Publication Date:
10 December 2019 (online)


In memory of Prof. Dieter Enders

Abstract

Bis-BINOL derivatives have proven highly useful in applications such as chemosensing or organocatalysis. In this account, we describe strategies for the linking of BINOL units via the 3-, 4-, or 5-positions, showing that unique synthetic strategies are necessary to address each position. We report the synthesis of suitable C 1-symmetric precursors, which are generated either by monohalogenation or by monodeprotection of C 2-symmetric starting materials, and their subsequent coupling to give linked bis-BINOL derivatives.

Supporting Information

 
  • References

  • 1 Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
  • 2 Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
    • 3a Pu L. Acc. Chem. Res. 2012; 45: 150
    • 3b Wang F, Nandhakumar R, Hu Y, Kim D, Kim KM, Yoon J. J. Org. Chem. 2013; 78: 11571
    • 3c Yu S, Pu L. Tetrahedron 2015; 71: 745
  • 4 Telfer SG, Kuroda R. Coord. Chem. Rev. 2003; 242: 33
    • 5a Brunel JM. Chem. Rev. 2005; 105: 857
    • 5b Brunel JM. Chem. Rev. 2007; 107: 857
    • 6a Cox PJ, Wang W, Snieckus V. Tetrahedron Lett. 1992; 33: 2253
    • 6b Yamashita Y, Ishitani H, Shimizu H, Kobayashi S. J. Am. Chem. Soc. 2002; 124: 3292
    • 7a Bisht R, Chaturvedi J, Pandey G, Chattopadhyay B. Org. Lett. 2019; 21: 6476
    • 7b Ahmed I, Clark DA. Org. Lett. 2014; 16: 4332
  • 8 Sogah GD. Y, Cram DJ. J. Am. Chem. Soc. 1979; 101: 3035
  • 9 Yang L, Yang F, Lan J, Gao G, You J, Su X. Org. Biomol. Chem. 2011; 9: 2618
    • 10a Huang H, Miao Q, Kang Y, Huang X, Xu J, Cheng Y. Bull. Chem. Soc. Jpn. 2008; 81: 1116
    • 10b Liu Y, Miao Q, Zhang S, Huang X, Zheng L, Cheng Y. Macromol. Chem. Phys. 2008; 209: 685
    • 10c Zhang S, Liu Y, Huang H, Zheng L, Wu L, Cheng Y. Synlett 2008; 853
    • 10d Wu L, Zheng L, Zong L, Xu J, Cheng Y. Tetrahedron 2008; 64: 2651
  • 11 Valente C, Choi E, Belowich ME, Doonan CJ, Li Q, Gasa TB, Botros YY, Yaghi OM, Stoddart JF. Chem. Commun. 2010; 4911
    • 12a Bandini M, Casolari S, Cozzi GP, Proni G, Schmohel E, Spada GP, Tagliavini E, Umani-Ronchi A. Eur. J. Org. Chem. 2000; 491
    • 12b Lustenberger P, Diederich F. Helv. Chim. Acta 2000; 83: 2865
    • 13a Li Z.-B, Lin J, Pu L. Angew. Chem. Int. Ed. 2005; 44: 1690
    • 13b Li Z.-B, Lin J, Sabat M, Hyacinth M, Pu L. J. Org. Chem. 2007; 72: 4905
    • 13c Li Z.-B, Lin J, Zhang H.-C, Sabat M, Hyacinth M, Pu L. J. Org. Chem. 2004; 69: 6284
    • 13d Lin J, Zhang H.-C, Pu L. Org. Lett. 2002; 4: 3297
    • 14a Yu J, Shi F, Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156
    • 14b Shibasaki M, Matsunaga S. Chem. Soc. Rev. 2006; 35: 269
    • 14c Mitra R, Niemeyer J. ChemCatChem 2018; 10: 1221
    • 15a Bähr A, Droz AS, Püntener M, Neidlein U, Anderson S, Seiler P, Diederich F. Helv. Chim. Acta 1998; 81: 1931
    • 15b Bähr A, Felber B, Schneider K, Diederich F. Helv. Chim. Acta 2000; 83: 1346
  • 16 Matsunaga S, Das J, Roels J, Vogl EM, Yamamoto N, Iida T, Yamaguchi K, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 2252
  • 17 Chen X.-H, Zhang W.-Q, Gong L.-Z. J. Am. Chem. Soc. 2008; 130: 5652
    • 18a Octa-Smolin F, Niemeyer J. Chem. Eur. J. 2018; 24: 16506
    • 18b Octa-Smolin F, Mitra R, Thiele M, Daniliuc CG, Stegemann L, Strassert C, Niemeyer J. Chem. Eur. J. 2017; 23: 10058
    • 18c Octa-Smolin F, Thiele M, Yadav R, Platzek A, Clever GH, Niemeyer J. Org. Lett. 2018; 20: 6153
  • 19 Kohlhaas M, Zähres M, Mayer C, Engeser M, Merten C, Niemeyer J. Chem. Commun. 2019; 3298
  • 20 Thölke S, Zhu H, Jansen D, Octa-Smolin F, Thiele M, Kaupmees K, Leito I, Grimme S, Niemeyer J. Eur. J. Org. Chem. 2019; 5190
    • 21a Wong FF, Chuang SH, Yang S.-c, Lin Y.-H, Tseng W.-C, Lin S.-K, Huang J.-J. Tetrahedron 2010; 66: 4068
    • 21b DiLauro AM, Seo W, Phillips ST. J. Org. Chem. 2011; 76: 7352
  • 22 Liu TJ, Chen YJ, Zhang KS, Wang D, Guo DW, Yang XZ. Chirality 2001; 13: 595
    • 23a Li Y, Li Q. Org. Lett. 2012; 14: 4362
    • 23b Lutzen A, Hapke M, Meyer S. Synthesis 2002; 2289
    • 23c Lutzen A, Thiemann F, Meyer S. Synthesis 2002; 2771
  • 24 We found that HCl-mediated deprotection of compounds 18d/e can lead to undesired 5-endo-dig cyclization, which can be avoided by using TMSBr; see: Octa-Smolin F, van der Vight F, Yadav R, Bhangu J, Soloviova K, Wolper C, Daniliuc CG, Strassert CA, Somnitz H, Jansen G, Niemeyer J. J. Org. Chem. 2018; 83: 14568
  • 25 Ngo HL, Lin W. J. Org. Chem. 2005; 70: 1177. However, this publication cites a Ph.D. thesis for the preparation of this compound: Lee, S. J.; Ph.D. Thesis, University of North Carolina at Chapel Hill, 2003. We obtained this thesis and could not find any synthetic procedure or characterization of monobromide 21