Download PDF
Synlett 2011(12): 1784-1785  
DOI: 10.1055/s-0030-1260936
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

Raghunath Chowdhury*
Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India
e-Mail: raghuch14@gmail.com;
Further Information

Publication History

Publication Date:
05 July 2011 (online)

   Permissions and Reprints All articles of this category

Introduction

Last decade witnessed an explosive growth in asymmetric organocatalysis. A large number of organocatalysts have been developed by different research groups. (S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine (CAS: 51207-66-0) is a versatile organocatalyst, which is commercially available or can be easily prepared from commercially available Cbz-(l)-proline (Scheme  [¹] ). [¹] It is known to catalyze many organic reactions, for example, the asymmetric ­aldol reaction, [²] [³] Michael reaction, [4-7] Mannich reaction, [8] and the domino reaction. [9] It is also used as a chiral ligand/additive in metal-mediated stereoselective organic syntheses. [¹0] [¹¹]

Scheme 1

    References

  • 1 Asami M. Bull. Chem. Soc. Jpn.  1990,  63:  721 
    CrossrefGoogle Scholar
  • 2a Saito S. Yamamoto H. Acc. Chem. Res.  2004,  37:  570 
    Google Scholar
  • 2b Mase N. Tanaka F. Barbas CF. Angew. Chem. Int. Ed.  2004,  43:  2420 
    Google Scholar
  • 2c Dambruoso P. Massi A. Dondoni A. Org. Lett.  2005,  7:  4657 
    Google Scholar
  • 3 Hayashi Y. Sekizawa H. Yamaguchi J. Gotoh H. J. Org. Chem.  2007,  72:  6493 
    CrossrefGoogle Scholar
  • 4 Mase N. Thayumanavan R. Tanaka F. Barbas CF. Org. Lett.  2004,  6:  2527 
    CrossrefPubMedGoogle Scholar
  • 5 Belot S. Sulzer-Mosse S. Kehrli S. Alexakis A. Chem. Commun.  2008,  4694 
    Google Scholar
  • 6a Chowdhury R. Ghosh SK. Org. Lett.  2009,  11:  3270 
    Google Scholar
  • 6b Chowdhury R. Ghosh SK. Synthesis  2011,  1936 
    Google Scholar
  • 7 Pitacco G. Attanasi OA. Crescentini LD. Favi G. Felluga F. Forzato C. Mantellini F. Nitti P. Valentin E. Zangrando E. Tetrahedron: Asymmetry  2010,  21:  617 
    CrossrefGoogle Scholar
  • 8a Zhuang W. Saaby S. Jørgensen KA. Angew. Chem. Int. Ed.  2004,  43:  4476 
    Google Scholar
  • 8b Li H. Fu A. Shi H. J. Mol. Catal. A: Chem.  2009,  303:  1 
    Google Scholar
  • 9a Rios R. Sundén H. Ibrahem I. Zhao G.-L. Córdova A. Tetrahedron Lett.  2006,  47:  8679 
    Google Scholar
  • 9b Rios R. Sundén H. Ibrahem I. Córdova A. Tetrahedron Lett.  2007,  48:  2181 
    Google Scholar
  • 10 Sharma AK. Maheshwary Y. Singh P. Singh KN. ARKIVOC  2010,  (ix):  54 
    Google Scholar
  • 11 Raja R. Thomas JM. Jones MD. Johnson BFG. Vaughan DEW. J. Am. Chem. Soc.  2003,  125:  14982 
    CrossrefGoogle Scholar