Download PDF
Synthesis 2005(4): 668-672  
DOI: 10.1055/s-2004-831211
PSP
© Georg Thieme Verlag Stuttgart · New York

Chemoselective Deprotection of Allylic Amines Catalyzed by Grubbs’ Carbene

Benito Alcaide*a, Pedro Almendros*b, José M. Alonsoa, Amparo Lunaa
a Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain
Fax: +34(91)3944103; e-Mail: alcaideb@quim.ucm.es;
b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Fax: +34(91)5644853; e-Mail: iqoa392@iqog.csic.es;
Further Information

Publication History

Received 5 May 2004
Publication Date:
21 October 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A commercially available ruthenium complex (first generation Grubbs’ carbene) was used for the catalytic deprotection of allylic amines (secondary as well as tertiary), by using for the first time reagents different from palladium catalysts. Interestingly, the catalytic system directs the reaction toward the selective deprotection of allylamines in the presence of allylic ethers.

Key words

amines - carbenes - catalytic cleavage - protecting groups - ruthenium

    References

  • 1a Greene TW. Wuts GM. In Protective Groups in Organic Synthesis   3rd. ed.:  Wiley; New York: 1999. 
    Google Scholar
  • 1b Kocienski PJ. Protecting Groups   3rd ed.:  Thieme; Stuttgart: 2003. 
    Google Scholar
  • 2 For an Ir-catalyzed deprotection of allylamides, see: Neugnot B. Cintrat J.-C. Rousseau B. Tetrahedron  2004,  60:  3575 
    CrossrefGoogle Scholar
  • 3 For a review, see: Guibé F. Tetrahedron  1998,  54:  2967 
    CrossrefGoogle Scholar
  • 4a Review: Alcaide B. Almendros P. Chem. Eur. J.  2003,  9:  1258 
    Google Scholar
  • 4b See also: Schmidt B. Angew. Chem. Int. Ed.  2003,  42:  4996 
    Google Scholar
  • 4c See also: Schmidt B. Eur. J. Org. Chem.  2004,  1865 
    Google Scholar
  • 4d For a recent paper, see: Hong SH. Day MW. Grubbs RH. J. Am. Chem. Soc.  2004,  126:  7414 
    Google Scholar
  • 5 Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc.  1996,  118:  100 
    Google Scholar
  • 6a Alcaide B. Almendros P. Alonso JM. Aly MF. Org. Lett.  2001,  3:  3781 
    CrossrefGoogle Scholar
  • 6b Alcaide B. Almendros P. Alonso JM. Chem. Eur. J.  2003,  9:  5793 
    CrossrefGoogle Scholar