Synlett 2012; 23(19): 2729-2734
DOI: 10.1055/s-0032-1317566
synpacts
© Georg Thieme Verlag Stuttgart · New York

Development of a Nonenzymatic Kinetic Resolution of α-Allenic Alcohols

Yan Wang
a  Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, P. R. of China   Fax: +862164166128   Email: rhong@sioc.ac.cn
,
Rob Hoen
b  GP Pharm, Isaac Peral 17 Polígon Camí Ral, 08850 Gavà (Barcelona), Spain
,
Ran Hong*
a  Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, P. R. of China   Fax: +862164166128   Email: rhong@sioc.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 18 September 2012

Accepted after revision: 22 October 2012

Publication Date:
13 November 2012 (online)

Abstract

This personal viewpoint lays out the development of a silver-catalyzed kinetic resolution of α-allenic alcohols inspired by the biomimetic synthesis of natural products. The corresponding selectivity factor (s) indicates that this resolution protocol can deliver chiral allenic alcohols and 2,5-dihydrofurans in high enantioselectivity with synthetically applicable isolated yields. The broad substrate scope makes it an attractive approach for building synthetically useful chiral building blocks. From the recent progress in allene chemistry, silver was considered as an anion metathesis reagent to prepare highly efficient Au catalysts. Our discovery of the unique reactivity of a chiral silver phosphate should stimulate more interesting discoveries in this field.

 
  • References and Notes

  • 1 Leandri G, Monti H, Bertrand M. Tetrahedron 1974; 30: 289
    • 2a Gelin R, Albrand M, Gelin S. C. R. Seances Acad. Sci., Ser. C 1969; 269: 241
    • 2b Gelin R, Gelin S, Albrand M. Bull. Soc. Chim. Fr. 1972; 1946
  • 3 Olsson LI, Claesson A. Synthesis 1979; 743

    • For recent reviews and monographs, see:
    • 4a Krause N, Hashmi AS. K. Modern Allene Chemistry . Wiley-VCH; Weinheim: 2004
    • 4b Rivera-Fuentes P, Diederich F. Angew. Chem. Int. Ed. 2012; 51: 2818
    • 4c Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074
    • 5a For a review on applications of allenic alcohol, see: Deng Y.-Q, Gu Z.-H, Ma S.-M. Chin. J. Org. Chem. (in Chinese) 2006; 26: 1468
    • 5b Friesen RW, Kolaczewska AE. J. Org. Chem. 1991; 56: 4888
    • 5c Friesen RW, Giroux A. Tetrahedron Lett. 1993; 34: 1867
    • 5d Friesen RW, Blouin MA. J. Org. Chem. 1993; 58: 1653
    • 5e Lautens M, Delanghe PH. M. J. Org. Chem. 1993; 58: 5037
    • 5f Marshall JA, Pinney KG. J. Org. Chem. 1993; 58: 7180
    • 5g Yoneda E, Kaneko T, Zhang S.-W, Onitsuka K, Takahashi S. Org. Lett. 2000; 2: 441
    • 6a Ma S, Zhao S. J. Am. Chem. Soc. 1999; 121: 7943
    • 6b Lee H.-Y, Sohn J.-H, Kim H.-Y. Tetrahedron Lett. 2001; 42: 1695
    • 6c Shibata T, Kadowaki S, Hirase M, Takagi K. Synlett 2003; 573
    • 6d Ohmura T, Suginome M. Org. Lett. 2006; 8: 2503
    • 7a Ma S, Hou H, Zhao S, Wang G. Synthesis 2002; 1643
    • 7b Crabbé P, Fillion H, André D, Luche J.-L. J. Chem. Soc., Chem. Commun. 1979; 859
    • 7c Crabbé P, Nassim B, Robert-Lopes M.-T. Org. Synth. 1985; 63: 203
    • 7d For the addition of axially chiral allenlyic silane to aldehyde, see: Marshall JA, Adams ND. J. Org. Chem. 1997; 62: 8976

    • For other indirect approaches through stereoselective ring-opening reactions, see:
    • 7e Kang S.-K, Kim D.-Y, Rho H.-S, Yoon S.-H, Ho P.-S. Synth. Commun. 1996; 26: 1485
    • 7f Fürstner A, Méndez M. Angew. Chem. Int. Ed. 2003; 42: 5355
    • 7g Miura T, Shimada M, Ku S.-Y, Tamai T, Murakami M. Angew. Chem. Int. Ed. 2007; 46: 7101
    • 8a Boldrini GP, Lodi L, Tagliavini E, Tarasco C, Trombini C, Umani-Ronchi A. J. Org. Chem. 1987; 52: 5447
    • 8b Corey EJ, Yu C.-M, Lee D.-H. J. Am. Chem. Soc. 1990; 112: 878
    • 8c Brown HC, Khire UR, Narla G. J. Org. Chem. 1995; 60: 8130
    • 8d Kulkarni SV, Brown HC. Tetrahedron Lett. 1996; 37: 4125
    • 8e A new efficient borane reagent was developed by the Soderquist group, see: Hernandez E, Soderquist JA. Org. Lett. 2005; 7: 5397
    • 8f Hernandez E, Burgos CH, Alicea E, Soderquist JA. Org. Lett. 2006; 8: 4089
    • 9a Yu C.-M, Yoon S.-K, Baek K, Lee J.-Y. Angew. Chem. Int. Ed. 1998; 37: 2392
    • 9b Inoue M, Nakada M. Angew. Chem. Int. Ed. 2006; 45: 252
    • 9c Xia G, Yamamoto H. J. Am. Chem. Soc. 2007; 129: 496
  • 10 Iseki K, Kuroki Y, Kobayashi Y. Tetrahedron: Asymmetry 1998; 9: 2889
  • 11 Nakajima M, Saito M, Hashimoto S. Tetrahedron: Asymmetry 2002; 13: 2449
  • 12 Reddy LR. Chem. Commun. 2012; 48: 9189
  • 13 Yu C.-M, Kim C, Kweon JH. Chem. Commun. 2004; 40: 2494
    • 14a Burgess K, Jennings LD. J. Am. Chem. Soc. 1990; 112: 7434
    • 14b Burgess K, Jennings LD. J. Am. Chem. Soc. 1991; 113: 6129
  • 15 Xu D, Li Z, Ma S. Chem.–Eur. J. 2002; 8: 5012
  • 16 Asikainen M, Krause N. Adv. Synth. Catal. 2009; 351: 2305
  • 17 Krause N, Hoffman-Röder A. Org. Lett. 2001; 3: 2537

    • For reviews, see:
    • 18a Gorin DJ, Toste FD. Nature 2007; 446: 395
    • 18b Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
    • 18c Krause N, Winter N. Chem. Rev. 2011; 111: 1994
    • 18d Pradal A, Toullec PY, Michelet V. Synthesis 2011; 1501
    • 18e Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
    • 19a Hamilton GL, Kang EJ, Mba M, Toste FD. Science 2007; 317: 496
    • 19b Aikawa K, Kojima M, Mikami K. Adv. Synth. Catal. 2010; 352: 3131
    • 19c LaLonde RL, Wang ZJ, Mba M, Lackner AD, Toste FD. Angew. Chem. Int. Ed. 2010; 49: 598
  • 20 Belmont P, Parker E. Eur. J. Org. Chem. 2009; 6075
  • 21 Wang Y, Zhu L, Zhang Y, Hong R. Angew. Chem. Int. Ed. 2011; 50: 2787
  • 22 Bates RW, Sridhar S. Synlett 2009; 1979
  • 23 Mi X, Wang Y, Zhu L, Hong R. Synthesis 2012; 44: 3432
    • 24a Wang Y, Zheng K, Hong R. J. Am. Chem. Soc. 2012; 134: 4096
    • 24b Chiral 2,5-dihydrofurans can be efficiently synthesized from axial allene alcohols. For a review, see: Krause N, Belting V, Deutsch C, Erdsack J, Fan H.-T, Gockel B, Hoffmann-Röder A, Morita N, Volz F. Pure Appl. Chem. 2008; 80: 1063 ; and references therein

      For excellent reviews on the application of chiral phosphoric acids (PAs), see:
    • 25a Akiyama T. Chem. Rev. 2007; 107: 5744
    • 25b Adair G, Mukherjee S, List B. Aldrichimica Acta 2008; 41: 31
    • 25c Terada M. Synthesis 2010; 1929
    • 26a Nagendrappa G, Devaprabhakara D. J. Organomet. Chem. 1969; 16: P73
    • 26b Nagendrappa G, Joshi GC, Devaprabhakara D. J. Organomet. Chem. 1971; 27: 421
    • 27a Brown TJ, Sugie A, Dickens MG, Widenhoefer RA. Organometallics 2010; 29: 4207
    • 27b Gandon V, Lemière G, Hours A, Fensterbank L, Malacria M. Angew. Chem. Int. Ed. 2008; 47: 7534
    • 28a Ozawa F, Kobo A, Hayashi T. J. Am. Chem. Soc. 1991; 113: 1417
    • 28b Ozawa F, Kubo A, Matsumoto Y, Hayashi T. Organometallics 1993; 12: 4188
    • 28c Loiseleur O, Meier P, Pfaltz A. Angew. Chem., Int. Ed. Engl. 1996; 35: 200
    • 28d Loiseleur O, Hayashi M, Schmees N, Pfaltz A. Synthesis 1997; 1338
    • 28e Yang Z, Zhou J. J. Am. Chem. Soc. 2012; 134: 11833

    • Recent reviews on this topic:
    • 28f Cartney DM, Guiry PJ. Chem. Soc. Rev. 2011; 40: 5122
    • 28g Diéguez M, Pàmies O. Isr. J. Chem. 2012; 52: 572
    • 29a Yoshida M, Shoji Y, Shishido K. Tetrahedron 2010; 66: 5053
    • 29b Yoshida M, Shoji Y, Shishido K. Org. Lett. 2009; 11: 1441
    • 29c Friesen RW, Bissada S. Tetrahedron Lett. 1994; 35: 5615
    • 29d Friesen RW, Giroux A. Can. J. Chem. 1994; 72: 1857
    • 30a Femenía-Ríos M, García-Pajón CM, Hernández-Galán R, Macías-Sánchez AJ, Collado IG. Bioorg. Med. Chem. Lett. 2006; 16: 5836
    • 30b Mancilla G, Femenía-Ríos M, Grande M, Hernández-Galán R, Macías-Sánchez AJ, Collado IG. Tetrahedron 2010; 66: 8086

      Recently, several interesting chiral silver phosphate-catalyzed reactions have been reported, see:
    • 31a Zhang Q.-W, Xiang K, Tu Y.-Q, Zhang S.-Y, Zhang X.-M, Zhao Y.-M, Zhang T.-C. Chem.–Asian J. 2012; 7: 894
    • 31b Zhang J.-W, Xu Z, Gu Q, Shi X.-X, Leng X.-B, You S.-L. Tetrahedron 2012; 68: 5263
    • 31c Shi S.-H, Huang F.-P, Zhu P, Dong Z.-W, Hui X.-P. Org. Lett. 2012; 14: 2010
    • 31d Rauniyar V, Wang ZJ, Burks HE, Toste FD. J. Am. Chem. Soc. 2011; 133: 8486
    • 31e For an early report on using chiral silver phosphate, see: Zhang Q.-W, Fan C.-A, Zhang H.-J, Tu Y.-Q, Zhao Y.-M, Gu P, Chen Z.-M. Angew. Chem. Int. Ed. 2009; 48: 8572

    • Very recent excellent reviews on chiral counteranion in asymmetric catalysis:
    • 31f Parra A, Reboredo S, MartínCastroa AM, Alemán J. Org. Biomol. Chem. 2012; 10: 5001
    • 31g Phipps RJ, Hamilton GL, Toste FD. Nature Chem. 2012; 4: 603