Download PDF
Synthesis 2009(2): 277-282  
DOI: 10.1055/s-0028-1083264
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Convenient Synthesis of Unsymmetrical Pinacols by Coupling of Structurally Similar Aromatic Aldehydes Mediated by Low-Valent Titanium

Xin-Fang Duan*, Jian-Xia Feng, Guo-Fu Zi, Zhan-Bin Zhang
Department of Chemistry, Beijing Normal University, Beijing, 100875, P. R. of China
Fax: +86(10)58802075; e-Mail: xinfangduan@vip.163.com;
Further Information

Publication History

Received 11 September 2008
Publication Date:
12 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

The one-pot, selective cross pinacol-type couplings between two structurally similar aromatic aldehydes promoted by low-valent titanium generated unsymmetrical pinacols in moderate to good isolated yields in an erythro/threo ratio of up to 91:9. This synthetic methodology significantly extends the scope of the cross pinacol-type couplings.

Key words

pinacol - pinacol-type coupling - cross coupling - McMurry­ coupling - low-valent titanium

    References

  • For reviews, see:
  • 1a Chatterjee A. Joshi NN. Tetrahedron  2006,  62:  12137 
    Google Scholar
  • 1b Gansäuer A. Bluhm H. Chem. Rev.  2000,  100:  2771 
    Google Scholar
  • 1c Fürstner A. Bogdanovic B. Angew. Chem., Int. Ed. Engl.  1996,  35:  2442 
    Google Scholar
  • 1d Wirth T. Angew. Chem., Int. Ed. Engl.  1996,  35:  61 
    Google Scholar
  • 1e McMurry JE. Chem. Rev.  1989,  89:  1513 
    Google Scholar
  • 1f Kahn BE. Rieke RD. Chem. Rev.  1988,  88:  733 
    Google Scholar
  • For selected reviews, see:
  • 2a Zaitsev AB. Adolfsson H. Synthesis  2006,  1725 
    Google Scholar
  • 2b Lohray BB. Tetrahedron: Asymmetry  1992,  3:  1317 
    Google Scholar
  • 2c Schroder M. Chem. Rev.  1980,  80:  187 
    Google Scholar
  • 3a Wang Z. Cui Y.-T. Xu Z.-B. Qu J. J. Org. Chem.  2008,  73:  2270 ; and references cited therein
    Google Scholar
  • 3b Lee SH. Lee EY. Yoo D.-W. Hong SJ. Lee JH. Kwak H. Lee YM. Kim J. Kim C. Lee J.-K. New J. Chem.  2007,  31:  1579 ; and references cited therein
    Google Scholar
  • 3c Gorzynski SJ. Synthesis  1984,  629 
    Google Scholar
  • 3d Behrens CH. Sharpless KB. Aldrichimica Acta  1983,  16:  67 
    Google Scholar
  • 4a Drutu I. Krygowski ES. Wood JL. J. Org. Chem.  2001,  66:  7025 
    Google Scholar
  • 4b Davis FA. Haque MS. Przeslawski RM. J. Org. Chem.  1989,  54:  2021 
    Google Scholar
  • 4c Fujita M. Hiyama T. J. Am. Chem. Soc.  1984,  106:  4629 ; and references cited therein
    Google Scholar
  • 5a Nicolaou KC. Yang Z. Liu JJ. Ueno H. Nantermet PG. Guy RK. Claiborne CF. Renauld J. Couladouros EA. Paulvannan K. Sorensen EJ. Nature  1994,  367:  630 
    Google Scholar
  • 5b Nicolaou KC. Yang Z. Liu JJ. Ueno H. Nantermet PG. Claiborne CF. Renauld J. Guy RK. Shibayama K. J. Am. Chem. Soc.  1995,  117:  645 
    Google Scholar
  • 6a McMurry JE. Dushin RG. J. Am. Chem. Soc.  1989,  111:  8928 
    Google Scholar
  • 6b McMurry JE. Dushin RG. J. Am. Chem. Soc.  1990,  112:  6942 
    Google Scholar
  • 7 Williams DR. Heidebrecht RW. J. Am. Chem. Soc.  2003,  125:  1843 
    CrossrefPubMedGoogle Scholar
  • 8 McMurry JE. Siemers NO. Tetrahedron Lett.  1994,  35:  4505 
    CrossrefGoogle Scholar
  • 9a Hou Z. Takamine K. Aoki O. Shiraishi H. Fujiwara Y. Taniguchi H. J. Org. Chem.  1988,  53:  6077 
    Google Scholar
  • 9b Freudenberger JH. Konradi AW. Pedersen SF. J. Am. Chem. Soc.  1989,  111:  8014 
    Google Scholar
  • 9c Konradi AW. Kemp SJ. Pedersen SF. J. Am. Chem. Soc.  1994,  116:  1316 
    Google Scholar
  • 9d Kang M. Park J. Pedersen SF. Synlett  1997,  41 
    Google Scholar
  • 9e Takai K. Morita R. Toratsu C. Angew. Chem. Int. Ed.  2001,  40:  1116 
    Google Scholar
  • 9f Takai K. Morita R. Matsushita H. Toratsu C. Chirality  2003,  15:  17 
    Google Scholar
  • 9g Groth U. Jung M. Vogel T. Chem. Eur. J.  2005,  11:  3127 
    Google Scholar
  • 9h Nair V. Ros S. Jayana CN. Rathb NP. Tetrahedron Lett.  2002,  43:  8967 
    Google Scholar
  • 9i Maekawa H. Yamamoto Y. Shimada H. Yonemura K. Nishiguchi I. Tetrahedron Lett.  2004,  45:  3869 
    Google Scholar
  • 9j Eilitz U. Böttcher C. Sieler J. Gockel S. Haas A. Burger K. Tetrahedron  2001,  57:  3921 
    Google Scholar
  • 10a Duan XF. Zeng J. Lü JW. Zhang ZB. J. Org. Chem.  2006,  71:  9873 
    Google Scholar
  • 10b Duan XF. Zeng J. Lü JW. Zhang ZB. Synthesis  2007,  713 
    Google Scholar
  • 10c Duan XF. Zeng J. Zhang ZB. Zi GF. J. Org. Chem.  2007,  72:  10283 
    Google Scholar
  • 11 Jenkins SS. Buck JS. Bigelow LA. J. Am. Chem. Soc.  1930,  52:  4495 
    CrossrefGoogle Scholar
  • 12 Uchida T. Kita Y. Maekawa H. Nishiguchi I. Tetrahedron  2006,  62:  3103 
    CrossrefGoogle Scholar
  • 13 Lion CJ. Vasselin DA. Schwalbe CH. Matthews CS. Stevens MFG. Westwell AD. Org. Biomol. Chem.  2005,  3:  3996 
    CrossrefGoogle Scholar
  • 14 Rochefort D. Bourbonnais R. Leech D. Paice MG. Chem. Commun.  2002,  1182 
    CrossrefGoogle Scholar
  • 15 Tiffeneau M. Jeanne L. Bull. Soc. Chim. Fr.  1931,  49:  1738 
    Google Scholar
  • 16 Mulzer J. Böhm I. Bats JW. Tetrahedron Lett.  1998,  39:  9643 
    CrossrefGoogle Scholar