Synthesis 2004(9): 1325-1330  
DOI: 10.1055/s-2004-822377
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of Optically Active Vicinal Diamine Arrays via Palladium-Catalyzed C-O to C-N Bond Transformation

Tetsuta Oshitari, Rumiko Akagi, Tadakatsu Mandai*
Department of Life Science, Kurashiki University of Science and the Arts, 2640 Nishinoura, Tsurajima, Kurashiki 712-8505, Japan
Fax: +81(86)4401062; e-Mail: ted@chem.kusa.ac.jp;
Further Information

Publication History

Received 15 April 2004
Publication Date:
18 May 2004 (online)

Abstract

Optically active vicinal diamine arrays have been provided efficiently via palladium-catalyzed C-O to C-N bond transformation.

    References

  • 1 Lucet D. Gall TL. Mioskowski C. Angew. Chem. Int. Ed.  1998,  37:  2580 
  • 2 Tsuritani N. Yamada K. Yoshikawa N. Shibasaki M. Chem. Lett.  2002,  276 ; and references therein
  • 3 Huang P.-Q. Liu L.-X. Wei B.-G. Ruan Y.-P. Org. Lett.  2003,  5:  1927 ; and references therein
  • 4 Yamazaki N. Atobe M. Kibayashi C. Tetrahedron Lett.  2002,  43:  7979 ; and references therein
  • For examples:
  • 5a Reetz MT. Jaeger R. Drewlies R. Hübel M. Angew. Chem., Int. Ed. Engl.  1991,  30:  103 
  • 5b Gonda J. Helland A.-C. Ernst B. Bellus D. Synthesis  1993,  729 
  • 5c Doherty AM. Kornberg BE. Reily MD. J. Org. Chem.  1993,  58:  795 
  • 6 Oshitari T. Mandai T. Synlett  2003,  2374 
  • Relevant works based on a similar concept have been reported; that is, palladium-catalyzed reaction of a vinyl epoxide or a 4-pentene-1,3-diol carbonate in the presence of an isocyanate provides an initial zwitterion of π-allyl-palladium complex whose oxygen anion is then trapped with isocyanate to give a second π-allylpalladium complex bearing a nitrogen nucleophile tethered to the oxygen. Intramolecular attack of the nitrogen nucleophile to the π-allylpalladium complex furnishes a five- or six-membered carbamate:
  • 7a Trost BM. Sudhakar AR. J. Am. Chem. Soc.  1987,  109:  3792 
  • 7b Trost BM. Sudhakar AR. J. Am. Chem. Soc.  1988,  110:  7933 
  • 7c Bando T. Harayama H. Fukazawa Y. Shiro M. Fugami K. Tanaka S. Tamaru Y. J. Org. Chem.  1994,  59:  1465 
  • 8 Dunn PJ. Häner R. Rapoport H. J. Org. Chem.  1990,  55:  5017