Synthesis 2019; 51(04): 865-873
DOI: 10.1055/s-0037-1611295
paper
© Georg Thieme Verlag Stuttgart · New York

Harvesting New Chiral Phosphotriesters by Phosphorylation of BINOL and Parent Bis-phenols

A. Ngo Ndimba
,
T. Roisnel
,
Univ Rennes, CNRS, ISCR UMR 6226, 35000 Rennes, France   Email: claudia.lalli@univ-rennes1.fr   Email: gilles.argouarch@univ-rennes1.fr
,
Univ Rennes, CNRS, ISCR UMR 6226, 35000 Rennes, France   Email: claudia.lalli@univ-rennes1.fr   Email: gilles.argouarch@univ-rennes1.fr
› Author Affiliations
This work was supported by Université de Rennes 1, CNRS, Rennes Métropole, and Région Bretagne.
Further Information

Publication History

Received: 31 August 2018

Accepted after revision: 04 October 2018

Publication Date:
25 October 2018 (eFirst)

Abstract

A systematic study on the phosphorylation of BINOL and other bis-phenols with chlorophosphates is described. An intriguing reactivity has been observed that is attributable to the hydroxyl group acidity and to the leaving group nucleofuge character within the phosphorylating agent used. By playing on these two parameters, new chiral monophosphotriesters, symmetrical homo-BINOL bisphosphates, and unsymmetrical non-homo-BINOL derivatives incorporating a non-chiral side unit, were synthesized selectively and in good yields.

Supporting Information

 
  • References

  • 1 Jacobsen EN, Pfaltz A, Yamamoto H. In Comprehensive Asymmetric catalysis . Springer-Verlag; Berlin, Hidelberg: 1999
    • 4a Erre G, Enthaler S, Junge K, Gladiali S, Beller M. Coord. Chem. Rev. 2008; 252: 471
    • 4b Pereira MM, Calvete MJ. F, Carrilho RM. B, Abreu AR. Chem. Soc. Rev. 2013; 42: 6990
    • 5a Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
    • 5b Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2017; 117: 10608
    • 5c Merad J, Lalli C, Bernadat G, Maury J, Masson G. Chem. Eur. J. 2018; 24: 3925
  • 6 Eberhardt L, Armspach D, Harrowfield J, Matt D. Chem. Soc. Rev. 2008; 37: 839
    • 7a Horiguchi H, Tsurugi H, Satoh T, Miura M. Adv. Synth. Catal. 2008; 350: 509
    • 7b Bouhachicha M, Ngo Ndimba A, Roisnel T, Lalli C, Argouarch G. New J. Chem. 2017; 41: 4767
    • 8a Nakatsuji H, Sawamura Y, Sakakura A, Ishihara K. Angew. Chem. Int. Ed. 2014; 53: 6974
    • 8b Lv J, Zhang Q, Zhong X, Luo S. J. Am. Chem. Soc. 2015; 137: 15576
    • 9a Dumoulin A, Lalli C, Masson G. Chem. Commun. 2015; 5383
    • 9b Lalli C, Dumoulin A, Lebée C, Drouet F, Guérineau V, Touboul D, Gandon V, Zhu J, Masson G. Chem. Eur. J. 2015; 21: 1704
    • 9c Lalli C, van de Weghe P. Chem. Commun. 2014; 7495
    • 10a Grelaud G, Tohmé A, Argouarch G, Roisnel T, Paul F. New J. Chem. 2011; 35: 2740
    • 10b Argouarch G, Grelaud G, Roisnel T, Humphrey MG, Paul F. Tetrahedron Lett. 2012; 53: 5015
    • 10c CordeiroJung T, Argouarch G, Van de Weghe P. Catal. Commun. 2016; 78: 52
    • 10d Surzhko V, Roisnel T, Le Grel B, Le Grel P, Lalli C, Argouarch G. Tetrahedron Lett. 2017; 58: 1343
  • 11 Slotin LA. Synthesis 1977; 737
    • 12a Sathe M, Gupta AK, Kaushik MP. Tetrahedron Lett. 2006; 47: 3107
    • 12b Kasemsuknimit A, Satyender A, Chavasiri W, Jang DO. Bull. Korean Chem. Soc. 2011; 32: 3486
    • 12c Xiong B, Feng X, Zhu L, Chen T, Zhou Y, Au C.-T, Yin S.-F. ACS Catal. 2015; 5: 537
    • 12d Xiong B, Hu C, Gu J, Yang C, Zhang P, Liu Y, Tang K. ChemistrySelect 2017; 2: 3376
    • 12e Xiong B, Ye Q, Feng X, Zhu L, Chen T, Zhou Y, Au C.-T, Yin S.-F. Tetrahedron 2014; 70: 9057
    • 12f Jones S, Selitsianos D. Org. Lett. 2002; 4: 3671
    • 12g Jones S, Selitsianos D, Thompson KJ, Toms SM. J. Org. Chem. 2003; 68: 5211
    • 12h Liu C.-Y, Pawar VD, Kao J.-Q, Chen C.-T. Adv. Synth. Catal. 2010; 352: 188
    • 12i Fu H, Yang T, Shang J.-Q, Zhou J.-L, Sun M, Li Y.-M. Org. Chem. Front. 2017; 4: 1777
    • 12j Yang Y, Qu C, Chen X, Sun K, Qu L, Bi W, Hu H, Li R, Jing C, Wei D, Wei S, Sun Y, Liu H, Zhao Y. Org. Lett. 2017; 19, 5864
    • 12k Xiong B, Zeng K, Zhang S, Zhou Y, Au C.-T. Tetrahedron 2015; 71: 9293
    • 12l Xiong B, Hu C, Li H, Zhou C, Zhang P, Liu Y, Tang K. Tetrahedron Lett. 2017; 58: 2428
    • 12m Xiong B, Wang G, Zhou C, Liu Y, Li J, Zhang P, Tang K. Phosphorus, Sulfur Silicon Relat. Elem. 2018; 193: 239
  • 13 Compound 6 has already been synthesized, this let us confirm the structure of the title product: Legrand O, Brunel JM, Constantieux T, Buono G. Chem. Eur. J. 1998; 4: 1061
  • 14 Compound 8 has already been described, see: Panmand DS, Tiwari AD, Panda SS, Monbaliu J.-CM, Beagle LK, Asiri AM, Stevens CV, Steel PJ, Hall CD, Katritzky AR. Tetrahedron Lett. 2014; 55: 5898
  • 15 Compound 9 has already been described, see: Voropai LM, Ruchkina NG, Milliaresi EE, Nifant’ev EE. Zh. Obshch. Khim. 1985; 55: 65
  • 16 For the synthesis of (S)-H8-BINOL, see: Pousse G, Devineau A, Dalla V, Humphreys L, Lasne M.-C, Rouden J, Blanchet J. Tetrahedron 2009; 65: 10617
  • 17 CCDC deposition numbers are: 1582040 for 8, 1582041 for 9, 1582042 for 14, 1582043 for 18, 1582044 for 19, 1582045 for 26. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 18 Egami H, Sato K, Asada J, Kawato Y, Hamashima Y. Tetrahedron 2015; 71: 6384
  • 19 The 1H NMR of compound 15 has already been described, see: Alloin F, El Tall O, Leprêtre J.-C, Cointeaux L, Boutafa L, Guindet J, Martin J.-F. Electrochim. Acta 2013; 112: 74
  • 20 Jonsson M, Lind J, Merényi G. J. Phys. Chem. A 2002; 106: 4758
    • 21a Billiot E, Macossay J, Thibodeaux S, Shamsi SA, Warner IM. Anal. Chem. 1998; 70: 1375
    • 21b Yudin AK, Martyn LJ. P, Pandiaraju S, Zheng J, Lough A. Org. Lett. 2000; 2: 41
    • 21c Mofaddel N, Krajian H, Villemin D, Desbène PL. J. Chromatogr., A 2008; 1211: 142
    • 21d Mofaddel N, Krajian H, Villemin D, Desbène PL. Talanta 2009; 78: 631
  • 22 Jaramillo P, Domingo LR, Pérez P. Chem. Phys. Lett. 2006; 420: 95 ; and references cited therein

    • For the synthesis of BINOL phosphorochloridate 17, see:
    • 23a An J, Wilson JM, An Y.-Z, Wiemer DF. J. Org. Chem. 1996; 61: 4040
    • 23b Sun H, Rajale T, Pan Y, Li G. Tetrahedron Lett. 2010; 51: 4403
  • 24 For the synthesis of H8-BINOL phosphorochloridate 19, see: Furuno H, Hayano T, Kambara T, Sugimoto Y, Hanamoto T, Tanaka Y, Jin YZ, Kagawa T, Inanaga J. Tetrahedron 2003; 59: 10509
  • 25 For the synthesis of the bisphosphite intermediate 25, see: Wilting J, Janssen M, Müller C, Lutz M, Spek AL, Vogt D. Adv. Synth. Catal. 2007; 349: 350