Synlett 2004(2): 0362-0364  
DOI: 10.1055/s-2003-44993
LETTER
© Georg Thieme Verlag Stuttgart · New York

Structural Revision of the Ring-Opened Product in the ZnCl2-Catalyzed Reactions of 1-Benzyl-2-phenylaziridine with Thiols

Yukiko Furuta, Takuya Kumamoto, Tsutomu Ishikawa*
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan
Fax: +81(43)2902910; e-Mail: benti@p.chiba-u.ac.jp;
Further Information

Publication History

Received 21 November 2003
Publication Date:
16 December 2003 (online)

Abstract

The reported β-amino sulfide structures for the products in the ZnCl2-catalyzed ring-opening reactions of 1-benzyl-2-phenyl­aziridine with thiols should be revised to 2-amino-1-phenylethyl sulfides from 2-amino-2-phenylethyl sulfides.

    References

  • Recent examples, see:
  • 1a Kang SH. Kim M. Ryu DH. Synlett  2003,  1149 
  • 1b Nishikawa T. Kajii S. Wada K. Ishikawa M. Isobe M. Synthesis  2002,  1658 
  • 1c Bhanu Prasad BA. Sanghi R. Singh VK. Tetrahedron  2002,  58:  7355 
  • 2 Hada K. Watanabe T. Isobe T. Ishikawa T. J. Am. Chem. Soc.  2001,  123:  7705 
  • 3 Wu J. Hou X.-L. Dai L.-X. J. Chem. Soc., Perkin Trans. 1  2001,  1314 
  • 4 Salvatore RN. Nagle AS. Jung KW. J. Org. Chem.  2002,  67:  674 
  • 5 Watson IDG. Yudin AK. J. Org. Chem.  2003,  68:  5160