Download PDF
Synthesis 2009(5): 860-863  
DOI: 10.1055/s-0028-1083297
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Rhodium(I)-Catalyzed Tandem Conjugate Additions

Cristina Navarro, Aurelio G. Csákÿ*
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain
Fax: +34(91)3945030; e-Mail: csaky@quim.ucm.es;
Further Information

Publication History

Received 30 July 2008
Publication Date:
19 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

1,2,3-Trisubstituted indanes are synthesized with high diastereoselectivity in favor of the all-trans products by the reaction of boronic acids with electron-deficient o-divinylbenzenes under rhodium(I) catalysis.

Key words

catalysis - Michael addition - tandem reactions - rhodium - synthesis

    References

  • 1 Zanoli P. Avallone R. Baraldi M. Phytother. Res.  1998,  12:  S114 
    CrossrefGoogle Scholar
  • 2 Melikian-Badalian A. inventors; WO  2002030915. 
  • 3 Cook CE. Wani MC. Jump JM. Lee Y.-W. Fail PA. Anderson SA. Gu Y.-Q. Petrow V. J. Med. Chem.  1995,  38:  753 
    CrossrefGoogle Scholar
  • 4 Alonso N. Caamaño O. Fernández F. García-Mera X. Morales M. Rodríguez-Borges JE. De Clercq E. Synthesis  2008,  1845 ; and references cited therein
    Article in Thieme ConnectGoogle Scholar
  • See for example:
  • 5a Elliott JD. Cousins RD. Gao A. Leber JD. Erhard KF. Nambi P. Elshourbagy NA. Kumar C. Lee JA. Bean JW. DeBrosse CW. Eggleston DS. Brooks DP. Feuerstein C. Gleason JG. Oeishoff CE. Ohlstein EH. J. Med. Chem.  1994,  37:  1553 
    Google Scholar
  • 5b Clark WM. Tickner-Eldridge AM. Huang GK. Pridgen LN. Olsen MA. Mills R. Lantos I. Baine NH. J. Am. Chem. Soc.  1998,  120:  4550 
    Google Scholar
  • 5c Clark WM. Curr. Opin. Drug Discovery Dev.  1999,  2:  565 
    Google Scholar
  • 5d Song ZJ. Zhao M. Frey L. Li J. Tan L. Chen CY. Tschaen DM. Tillyer R. Grabowski EJJ. Volante R. Reider PJ. Org. Lett.  2001,  3:  3357 
    Google Scholar
  • 5e Langleben D. Clin. Chest Med.  2007,  28:  117 
    Google Scholar
  • For general reviews on conjugate addition reactions catalyzed by Rh(I), see:
  • 6a Hayashi T. Synlett  2001,  879 
    Google Scholar
  • 6b Fagnou K. Lautens M. Chem. Rev.  2003,  103:  169 
    Google Scholar
  • 6c Hayashi T. Yamasaki K. Chem. Rev.  2003,  103:  2829 
    Google Scholar
  • 6d Hayashi T. Pure Appl. Chem.  2004,  76:  465 
    Google Scholar
  • 6e Yoshida K. Hayashi T. In Modern Rhodium-Catalyzed Organic Reactions   Evans PA. Wiley-VCH; Weinheim: 2005.  Chap. 3. p.55 
    Google Scholar
  • 7 For sequential carborhodations triggered by the conjugate addition of organoborons to electron-deficient alkenes under Rh(I) catalysis, see: Miura T. Murakami M. Chem. Commun.  2007,  217 
    CrossrefGoogle Scholar
  • 8 Navarro C. Csákÿ AG. Org. Lett.  2008,  10:  217 
    CrossrefGoogle Scholar
  • For review see:
  • 9a Hayashi T. Bull. Chem. Soc. Jpn.  2004,  77:  13 
    Google Scholar
  • See also:
  • 9b Nishikata T. Yamamoto Y. Miyaura N. Angew. Chem. Int. Ed.  2003,  42:  2768 
    Google Scholar
  • 9c Nishikata T. Yamamoto Y. Miyaura N. Organometallics  2004,  23:  4317 
    Google Scholar
  • 9d Gini F. Hessen B. Minnaard AJ. Org. Lett.  2005,  7:  5309 
    Google Scholar
  • 9e Lu X. Lin S. J. Org. Chem.  2005,  70:  9651 
    Google Scholar
  • 9f Yamamoto Y. Iizuka M. Ohta T. Ito Y. Chem. Lett.  2006,  35:  198 
    Google Scholar
  • 9g He P. Lu Y. Dong C.-G. Hu Q.-S. Org. Lett.  2007,  9:  343 
    Google Scholar
  • 9h Horiguchi H. Tsurugi H. Satoh T. Miura M. J. Org. Chem.  2008,  73:  1590 
    Google Scholar