Synthesis 2013; 45(5): 592-595
DOI: 10.1055/s-0032-1317949
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A General Approach to Terminal Allenols

Jinqiang Kuang
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
,
Xi Xie
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
,
Shengming Ma*
a   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Linglin Lu, Shanghai 200032, P. R. of China   Fax: +86(21)62609305   eMail: masm@sioc.ac.cn
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Publikationsverlauf

Received: 11. Oktober 2012

Accepted after revision: 03. Dezember 2012

Publikationsdatum:
24. Januar 2013 (online)


Abstract

We have demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,2-addition with aldehydes or ketones, and subsequent base-catalyzed triple-bond migration.

Supporting Information

 
  • References

  • 1 For a recent monograph, see: Modern Allene Chemistry . Vol. 1 and 2. Krause N, Hashmi AS. K. Wiley-VCH; Weinheim: 2004

    • For reviews, see:
    • 2a Wang KK. Chem. Rev. 1996; 96: 207
    • 2b Marshall JA. Chem. Rev. 2000; 100: 3163
    • 2c Hashmi AS. K. Angew. Chem. Int. Ed. 2000; 39: 3590
    • 2d Zimmer R, Dinesh CU, Nandanan E, Khan FA. Chem. Rev. 2000; 100: 3067
    • 2e Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
    • 2f Bates RW, Satcharoen V. Chem. Soc. Rev. 2002; 31: 12
    • 2g Ma S. Acc. Chem. Res. 2003; 36: 701
    • 2h Sydnes L. Chem. Rev. 2003; 103: 1133
    • 2i Brandsma L, Nedolya NA. Synthesis 2004; 735
    • 2j Tius MA. Acc. Chem. Res. 2003; 36: 284
    • 2k Wei LL, Xiong H, Hsung RP. Acc. Chem. Res. 2003; 36: 773
    • 2l Ma S. Palladium-Catalyzed Two- or Three-Component Cyclization of Functionalized Allenes. In Palladium in Organic Synthesis. Tsuji J. Springer; Berlin: 2005: 183-210
    • 2m Ma S. Chem. Rev. 2005; 105: 2829
    • 2n Ma S. Aldrichimica Acta 2007; 40: 91
    • 2o Kim H, Williams LJ. Curr. Opin. Drug Discovery Dev. 2008; 11: 870
    • 2p Brasholz M, Reissig H.-U, Zimmer R. Acc. Chem. Res. 2009; 42: 45
    • 2q Ma S. Acc. Chem. Res. 2009; 42: 1679

      For reviews on natural products and pharmaceuticals containing an allene unit, see:
    • 3a Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
    • 3b Krause N, Hoffmann-Röder A In Modern Allene Chemistry . Krause N, Hashmi AS. K. Wiley-VCH; Weinheim: 2004. Chap. 18
    • 3c Also see p. 891 of ref. 2o.

      For recent reviews or highlights on the synthesis of allenes, see:
    • 4a Krause N, Hoffmann-Röder A. Tetrahedron 2004; 60: 11671
    • 4b Hammond GB. ACS Symp. Ser. 2005; 911: 204
    • 4c Brummond KM, Deforrest JE. Synthesis 2007; 795
    • 4d Ogasawara M. Tetrahedron: Asymmetry 2009; 20: 259
    • 4e Modern Allene Chemistry . Krause N, Hashmi AS. K. Wiley-VCH; Weinheim: 2004. Chap. 1-8
    • 4f Yu S, Ma S. Chem. Commun. 2011; 47: 5384
    • 5a Crabbé P, Fillion H, André D, Luche J.-L. J. Chem. Soc., Chem. Commun. 1979; 859
    • 5b Searles S, Li Y, Nassim B, Lopes M.-TR, Tran PT, Crabbé P. J. Chem. Soc., Perkin Trans. 1 1984; 747
    • 5c Ma S, Hou H, Zhao S, Wang G. Synthesis 2002; 1643
    • 5d Kazmaier U, Lucas S, Klein M. J. Org. Chem. 2006; 71: 2429
    • 5e Trost BM, Pinkerton AB, Seidel M. J. Am. Chem. Soc. 2001; 123: 12466
    • 5f Kuang J, Ma S. J. Org. Chem. 2009; 74: 1763
    • 5g Chen B, Wang N, Fan W, Ma S. Org. Biomol. Chem. 2012; 10: 8645

    • For the reaction with aldehydes to form 1,3-disubstituted allenes, see:
    • 5h Kuang J, Ma S. J. Am. Chem. Soc. 2010; 132: 1786
    • 5i Kuang J, Luo H, Ma S. Adv. Synth. Catal. 2012; 354: 933
    • 5j Ye J, Li S, Chen B, Fan W, Kuang J, Liu J, Liu Y, Miao B, Wan B, Wang Y, Xie X, Yu Q, Yuan W, Ma S. Org. Lett. 2012; 14: 1346
    • 5k Ye J, Fan W, Ma S. Chem. Eur. J. 2013; 19: 716
    • 6a Olsson L.-I, Claesson A. Synthesis 1979; 743
    • 6b Nikam SS, Chu K.-H, Wang KK. J. Org. Chem. 1986; 51: 745
    • 6c Marshall JA, Wang X. J. Org. Chem. 1990; 55: 2995
    • 6d Marshall JA, Pinney KG. J. Org. Chem. 1993; 58: 7180
    • 6e Marshall JA, Sehon CA. J. Org. Chem. 1995; 60: 5966
    • 6f Ma S, Gao W. Tetrahedron Lett. 2000; 41: 8933
    • 6g Hoffmann-Röder A, Krause N. Org. Lett. 2001; 3: 2537
  • 7 Ma S, Gao W. J. Org. Chem. 2002; 67: 6104
    • 8a Friesen RW, Blouin M. J. Org. Chem. 1993; 58: 1653
    • 8b Ma S, Zhao S. J. Am. Chem. Soc. 1999; 121: 7943
    • 9a Fu C, Li J, Ma S. Chem. Commun. 2005; 4119
    • 9b Li J, Fu C, Chen G, Chai G, Ma S. Adv. Synth. Catal. 2008; 350: 1376
    • 10a Lu Z, Ma S. Adv. Synth. Catal. 2007; 349: 1225
    • 10b Cheng X, Jiang X, Yu Y, Ma S. J. Org. Chem. 2008; 73: 8960
    • 10c Li J, Kong W, Yu Y, Fu C, Ma S. J. Org. Chem. 2009; 74: 8733
    • 10d Li Q, Jiang X, Fu C, Ma S. Org. Lett. 2011; 13: 466
    • 11a Wotiz JH, Mancuso DE. J. Org. Chem. 1957; 22: 207
    • 11b Mukaiyama T, Harada T. Chem. Lett. 1981; 621
    • 11c Isaac MB, Chan T.-H. J. Chem. Soc., Chem. Commun. 1995; 1003
    • 12a Place P, Delbecq F, Gore J. Tetrahedron Lett. 1978; 3801
    • 12b Flahaut J, Miginiac P. Helv. Chim. Acta 1978; 61: 2275
    • 12c Girard P, Namy JL, Kagan HB. J. Am. Chem. Soc. 1980; 102: 2693

      For some reports on the synthesis of optically active allenols, see:
    • 13a Yu C.-M, Kim C, Kweon J.-H. Chem. Commun. 2004; 2494
    • 13b Corey EJ, Yu C.-M, Lee D.-H. J. Am. Chem. Soc. 1990; 112: 878
    • 13c Marshall JA, Perkins J. J. Org. Chem. 1994; 59: 3509
    • 13d Marshall JA, Adams ND. J. Org. Chem. 1997; 62: 8976
    • 13e Hernandez E, Soderquist JA. Org. Lett. 2005; 7: 5397
    • 13f Hernandez E, Burgos CH, Alicea E, Soderquist JA. Org. Lett. 2006; 8: 4089
    • 13g Yu C.-M, Yoon S.-K, Baek K, Lee J.-Y. Angew. Chem. Int. Ed. 1998; 37: 2392
    • 13h Schultz-Fademrecht C, Wibbeling B, Fröhlich R, Hoppe D. Org. Lett. 2001; 3: 1221
    • 13i Inoue M, Nakada M. Angew. Chem. Int. Ed. 2006; 45: 252
    • 13j Xia G, Yamamoto H. J. Am. Chem. Soc. 2007; 129: 496
    • 13k Marshall JA, Tang Y. J. Org. Chem. 1993; 58: 3233
    • 13l Xu D, Li Z, Ma S. Chem. Eur. J. 2002; 8: 5012
    • 13m Xu D, Li Z, Ma S. Tetrahedron: Asymmetry 2003; 14: 3657
  • 14 Vaughn TH, Hennion GF, Vogt RR, Nieuwland JA. J. Org. Chem. 1937; 2: 1
  • 15 Fantazier RM, Poutsma ML. J. Am. Chem. Soc. 1968; 90: 5490
    • 16a Brown CA, Yamashita A. J. Am. Chem. Soc. 1975; 97: 891
    • 16b Abrams SR, Shaw AC. Org. Synth. Coll. Vol. VIII . John Wiley & Sons; New York: 1993: 146
  • 17 Xu D, Li Z, Ma S. Tetrahedron Lett. 2003; 44: 6343