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Synlett 2010(12): 1789-1792  
DOI: 10.1055/s-0030-1258109
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Tetrahydrofurans from Substituted Hex-5-yne-1,4-diols

Carolin Schwehm, Max Wohland, Martin E. Maier*
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295135; e-Mail: martin.e.maier@uni-tuebingen.de;
Further Information

Publication History

Received 16 April 2010
Publication Date:
30 June 2010 (online)

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Abstract

It was discovered that substituted hex-5-yne-1,4-diols like 16, 28, and 30 undergo a domino sequence of Meyer-Schuster rearrangement followed by Michael addition forming 2,5-disubstituted tetrahydrofurans in presence of PtCl2.

Key words

alkynes - domino reaction - Michael addition - organometallic reagents - rearrangement

    References

  • 1 For a recent review, see: Hintermann L. Labonne A. Synthesis  2007,  1121 
    Article in Thieme ConnectGoogle Scholar
  • For some reviews, see:
  • 2a Hashmi ASK. Chem. Rev.  2007,  107:  3180 
    Google Scholar
  • 2b Fürstner A. Davies PW. Angew. Chem. Int. Ed.  2007,  46:  3410 ; Angew. Chem. 2007, 119, 3478
    Google Scholar
  • 2c Marion N. Nolan SP. Angew. Chem. Int. Ed.  2007,  46:  2750 ; Angew. Chem. 2007, 119, 2806
    Google Scholar
  • 2d Jimenez-Nunez E. Echavarren AM. Chem. Commun.  2007,  333 
    Google Scholar
  • 2e Arcadi A. Chem. Rev.  2008,  108:  3266 
    Google Scholar
  • 2f Gorin DJ. Sherry BD. Toste FD. Chem. Rev.  2008,  108:  3351 
    Google Scholar
  • 2g Patil NT. Yamamoto Y. Chem. Rev.  2008,  108:  3395 
    Google Scholar
  • 2h Melchiorre P. Marigo M. Carlone A. Bartoli G. Angew. Chem. Int. Ed.  2008,  47:  6138 ; Angew. Chem. 2008, 120, 6232
    Google Scholar
  • 2i Bongers N. Krause N. Angew. Chem. Int. Ed.  2008,  47:  2178 ; Angew. Chem. 2008, 120, 2208
    Google Scholar
  • 2j Li Z. Brouwer C. He C. Chem. Rev.  2008,  108:  3239 
    Google Scholar
  • 2k Fürstner A. Chem. Soc. Rev.  2009,  38:  3208 
    Google Scholar
  • 3a Kang J.-E. Shin S. Synlett  2006,  717 
    Google Scholar
  • 3b Belting V. Krause N. Org. Lett.  2006,  8:  4489 
    Google Scholar
  • 3c Wilckens K. Uhlemann M. Czekelius C. Chem. Eur. J.  2009,  15:  13323 
    Google Scholar
  • See, for example:
  • 4a Fürstner A. Hannen P. Chem. Eur. J.  2006,  12:  3006 
    Google Scholar
  • 4b Jimenez-Nunez E. Molawi K. Echavarren AM. Chem. Commun.  2009,  7327 
    Google Scholar
  • 4c Kirsch SF. Synthesis  2008,  3183 
    Google Scholar
  • 5a Liu B. De Brabander JK. Org. Lett.  2006,  8:  4907 
    Google Scholar
  • 5b Trost BM. Weiss AH. Angew. Chem. Int. Ed.  2007,  46:  7664; Angew. Chem. 2007, 119, 7808 
    Google Scholar
  • 5c Aponick A. Li C.-Y. Palmes JA. Org. Lett.  2009,  11:  121 
    Google Scholar
  • 6 Antoniotti S. Genin E. Michelet V. Genêt J.-P. J. Am. Chem. Soc.  2005,  127:  9976 
    Google Scholar
  • For some recent reviews, covering the synthesis of spiroacetals, see:
  • 7a Perron F. Albizati KF. Chem. Rev.  1989,  89:  1617 
    Google Scholar
  • 7b Yeung K.-S. Paterson I. Chem. Rev.  2005,  105:  4237 
    Google Scholar
  • 7c Aho JE. Pihko PM. Rissa TK. Chem. Rev.  2005,  105:  4406 
    Google Scholar
  • 7d Kiyota H. Top. Heterocycl. Chem.  2006,  5:  65 
    Google Scholar
  • 7e El Sous M. Ganame D. Zanatta S. Rizzacasa MA. ARKIVOC  2006,  105 
    Google Scholar
  • 8 Barun O. Kumar K. Sommer S. Langerak A. Mayer TU. Müller O. Waldmann H. Eur. J. Org. Chem.  2005,  4773 
    CrossrefGoogle Scholar
  • 9 Niggemann J. Bedorf N. Flörke U. Steinmetz H. Gerth K. Reichenbach H. Höfle G. Eur. J. Org. Chem.  2005,  5013 
    CrossrefGoogle Scholar
  • 10a Lorenz M. Kalesse M. Tetrahedron Lett.  2007,  48:  2905 
    Google Scholar
  • 10b Lorenz M. Kalesse M. Org. Lett.  2008,  10:  4371 
    Google Scholar
  • 10c Lorenz M. Bluhm N. Kalesse M. Synthesis  2009,  3061 
    Google Scholar
  • 11a Paterson I. Findlay AD. Anderson EA. Angew. Chem. Int. Ed.  2007,  46:  6699 ; Angew. Chem. 2007, 119, 6819
    Google Scholar
  • 11b Paterson I. Findlay AD. Noti C. Chem. Commun.  2008,  6408 
    Google Scholar
  • 11c Paterson I. Findlay AD. Noti C. Chem. Asian J.  2009,  4:  594 
    Google Scholar
  • 12 Kitamura M. Tokunaga M. Ohkuma T. Noyori R. Org. Synth.  1992,  71:  1 ; Org. Synth., Coll. Vol. IX; 1998, 589
    Google Scholar
  • 13 Ono M. Nakamura H. Konno F. Akita H. Tetrahedron: Asymmetry  2000,  11:  2753 
    CrossrefGoogle Scholar
  • 14 Moore CG. Murphy PJ. Williams HL. McGown AT. Smith NK. Tetrahedron  2007,  63:  11771 
    CrossrefGoogle Scholar
  • 15a Wilk BK. Synth. Commun.  1993,  23:  2481 
    Google Scholar
  • 15b Aesa MC. Baán G. Novák L. Szántay C. Synth. Commun.  1995,  25:  1545 
    Google Scholar
  • 16 Pietruszka J. Witt A. Synthesis  2006,  4266 
    Article in Thieme ConnectGoogle Scholar
  • 17a Frantz DE. Fässler R. Carreira EM. J. Am. Chem. Soc.  2000,  122:  1806 
    Google Scholar
  • 17b Sasaki H. Boyall D. Carreira EM. Helv. Chim. Acta  2001,  84:  964 
    Google Scholar
  • 17c Boyall D. Frantz DE. Carreira EM. Org. Lett.  2002,  4:  2605 
    Google Scholar
  • 18 In this paper a domino redox-isomerization-oxa-Michael reaction was used to prepare pyrans: Trost BM. Gutierrez AC. Livingston RC. Org. Lett.  2009,  11:  2539 
    Google Scholar
  • 19a Engel DA. Dudley GB. Org. Lett.  2006,  8:  4027 
    Google Scholar
  • 19b Egi M. Yamaguchi Y. Fujiwara N. Akai S. Org. Lett.  2008,  10:  1867 
    Google Scholar
  • 19c Stefanoni M. Luparia M. Porta A. Zanoni G. Vidari G. Chem. Eur. J.  2009,  15:  3940 
    Google Scholar
  • 19d Ramón RS. Marion N. Nolan SP. Tetrahedron  2009,  65:  1767 
    Google Scholar
  • 20a Mangion IK. MacMillan DWC. J. Am. Chem. Soc.  2005,  127:  3696 
    Google Scholar
  • 20b Varseev GN. Maier ME. Org. Lett.  2007,  9:  1461 
    Google Scholar
  • 20c Kondekar NB. Kumar P. Org. Lett.  2009,  11:  2611 
    Google Scholar
  • 21 Suffert J. Toussaint D. J. Org. Chem.  1995,  60:  3550 
    CrossrefGoogle Scholar