PDF icon Download PDF
Synlett 2012(3): 468-472  
DOI: 10.1055/s-0031-1290313
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Vinylogous Aldol Reaction Triggered by Tetrabutylammonium Fluoride: A Highly Regioselective and Diastereoselective Addition of Cyclic β-Haloenals to Aromatic Aldehydes

Jingli Zhang, Lianghu Gu, Yuefa Gong*
School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China
Fax: +86(27)87543632; e-Mail: gongyf@mail.hust.edu.cn;
Further Information

Publication History

Received 1 November 2011
Publication Date:
19 January 2012 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

A new type of direct vinylogous aldol addition between cyclic β-haloenals and aromatic aldehydes promoted by TBAF has been developed. The reaction was carried out under mild conditions to provide highly functionalized δ-hydroxy-β-halo-α,β-unsaturated aldehydes with high diastereomeric ratios and low to good yields.

Key words

direct vinylogous aldol reaction - TBAF - cyclic β-haloenals - regio- and diastereoselectivity - homoallylic alcohols

    References and Notes

  • For VA reaction in synthesis of natural products and biologically active compounds, see:
  • 1a Abramite JA. Sammakia T. Org. Lett.  2007,  9:  2103 
    Search in Google Scholar
  • 1b Jahn U. Dinca E. Chem. Eur. J.  2009,  15:  58 
    Search in Google Scholar
  • 1c Miesch L. Rietsch V. Welsch T. Miesch M. Tetrahedron Lett.  2008,  49:  5053 
    Search in Google Scholar
  • 1d Vaz B. Alvarez R. Brückner R. De Lera AR. Org. Lett.  2005,  7:  545 
    Search in Google Scholar
  • 1e Wu TJ. Huang PQ. Tetrahedron Lett.  2008,  49:  383 
    Search in Google Scholar
  • 1f Liu G. Wu TJ. Ruan YP. Huang PQ. Chem. Eur. J.  2010,  16:  5755 
    Search in Google Scholar
  • 1g Hunter R. Rees-Jones SCM. Su H. Tetrahedron Lett.  2007,  48:  2819 
    Search in Google Scholar
  • 1h Nomiya M. Murakami T. Noboru T. Okuno T. Harada Y. Hashimoto M. J. Org. Chem.  2008,  73:  5039 
    Search in Google Scholar
  • 1i Teixeira RR. Barbosa LCA. Santana JO. Veloso DP. Ellena J. Doriguetto AC. Drew MGB. Ismail FMD. J. Mol. Struct.  2007,  837:  197 
    Search in Google Scholar
  • 1j Barbosa LCA. Rocha ME. Teixeira RR. Maltha CRA. Forlani G. J. Agric. Food. Chem.  2007,  55:  8562 
    Search in Google Scholar
  • 1k Boukouvalas J. McCann LC. Tetrahedron Lett.  2010,  51:  4636 
    Search in Google Scholar
  • 1l Paterson I. Davies RDM. Marquez R. Angew. Chem. Int. Ed.  2001,  40:  603 
    Search in Google Scholar
  • 1m Tiseni PS. Peters R. Org. Lett.  2008,  10:  2019 
    Search in Google Scholar
  • For reviews of VA reaction, see:
  • 2a Casiraghi G. Zanardi F. Appendino G. Rassu G. Chem. Rev.  2000,  100:  1929 
    Search in Google Scholar
  • 2b Denmark SE. Heemstra JR. Beutner GL. Angew. Chem. Int. Ed.  2005,  44:  4682 
    Search in Google Scholar
  • 2c Kalesse M. Top. Curr. Chem.  2005,  244:  43 
    Search in Google Scholar
  • 2d Casiraghi G. Battistini L. Curti C. Rassu G. Zanardi F. Chem. Rev.  2011,  111:  3076 
    Search in Google Scholar
  • For VMA reactions, see:
  • 3a Shinoyama M. Shirokawa S.-i. Nakazaki A. Kobayashi S. Org. Lett.  2009,  11:  1277 
    Search in Google Scholar
  • 3b Shirokawa S.-i. Kamiyama M. Nakamura T. Okada M. Nakazaki A. Hosokawa S. Kobayashi S. J. Am. Chem. Soc.  2004,  126:  13604 
    Search in Google Scholar
  • 3c Ehrlich G. Hassfeld J. Eggert U. Kalesse M. Chem. Eur. J.  2008,  14:  2232 
    Search in Google Scholar
  • 3d Hassfeld J. Kalesse M. Tetrahedron Lett.  2002,  43:  5093 
    Search in Google Scholar
  • 3e Bhatt U. Christmann M. Quitschalle M. Claus E. Kalesse M. J. Org. Chem.  2001,  66:  1885 
    Search in Google Scholar
  • 3f Hassfeld J. Christmann M. Kalesse M. Org. Lett.  2001,  3:  3561 
    Search in Google Scholar
  • 3g Christmann M. Bhatt U. Quitschalle M. Claus E. Kalesse M. Angew. Chem. Int. Ed.  2000,  39:  4364 
    Search in Google Scholar
  • 3h Perreault S. Spino C. Org. Lett.  2006,  8:  4385 
    Search in Google Scholar
  • 3i Eissler S. Nahrwold M. Neumann B. Stammler H.-G. Sewald N. Org. Lett.  2007,  9:  817 
    Search in Google Scholar
  • 3j Zou B. Long K. Ma D. Org. Lett.  2005,  7:  4237 
    Search in Google Scholar
  • 3k Suenaga K. Mutou T. Shibata T. Itoh T. Fujita T. Takada N. Hayamizu K. Takagi M. Irifune T. Kigoshi H. Yamada K. Tetrahedron  2004,  60:  8509 
    Search in Google Scholar
  • 3l Hassfeld J. Kalesse M. Synlett  2002,  2007 
  • For direct VA reactions, see:
  • 4a Bella M. Piancatelli G. Squarcia A. Trolli C. Tetrahedron Lett.  2000,  41:  3669 
    Search in Google Scholar
  • 4b Bella M. Piancatelli G. Squarcia A. Tetrahedron  2001,  57:  4429 
    Search in Google Scholar
  • 4c Sarma KD. Zhang J. Curran TT. J. Org. Chem.  2007,  72:  3311 
    Search in Google Scholar
  • For asymmetric direct VA reactions, see:
  • 5a Yang Y. Zheng K. Zhao J. Lin L. Liu X. Feng X. J. Org. Chem.  2010,  75:  5382 
    Search in Google Scholar
  • 5b Ube H. Shimada N. Terada M. Angew. Chem. Int. Ed.  2010,  49:  1858 
    Search in Google Scholar
  • 5c Luo J. Wang H. Han X. Xu L.-W. Kwiatkowski J. Huang K.-W. Lu Y. Angew. Chem. Int. Ed.  2011,  50:  1861 
    Search in Google Scholar
  • 5d Pansare SV. Paul EK. Chem. Commun.  2011,  47:  1027 
    Search in Google Scholar
  • 6 Adamo MFA. Suresh S. Tetrahedron  2009,  65:  990 
    Search in Google Scholar
  • 7a Aponte JC. Hammond GB. Xu B. J. Org. Chem.  2009,  74:  4623 
    Search in Google Scholar
  • 7b Xu B. Hammond GB. Angew. Chem. Int. Ed.  2008,  47:  689 
    Search in Google Scholar
  • 8 Lautens M. Han W. Liu JH.-C. J. Am. Chem. Soc.  2003,  125:  4028 
    Search in Google Scholar
  • 9a Liu K. Chougnet A. Woggon W.-D. Angew. Chew. Int. Ed.  2008,  47:  5827 
    Search in Google Scholar
  • 9b Lesch B. Toräng J. Vanderheiden S. Bräse S. Adv. Synth. Catal.  2005,  347:  555 
    Search in Google Scholar
  • 9c Volz N. Bröhmer MC. Nieger M. Bräse S. Synlett  2009,  550 
  • 10a Saito S. Shiozawa M. Ito M. Yamamoto H. J. Am. Chem. Soc.  1998,  120:  813 
    Search in Google Scholar
  • 10b Saito S. Nagahara T. Shiozawa M. Nakadai M. Yamamoto H. J. Am. Chem. Soc.  2003,  125:  6200 
    Search in Google Scholar
  • 11 Zhang J.-L. Gong Y.-F. Org. Lett.  2011,  13:  176 
    Search in Google Scholar
  • 13a Hawkinson DC. Wang Y. J. Org. Chem.  2007,  72:  3592 
    Search in Google Scholar
  • 13b Whalen DL. Weimaster JF. Ross AM. Radhe R. J. Am. Chem. Soc.  1976,  98:  7319 
    Search in Google Scholar
12

CCDC 825960 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.