The First Example of Catalytic Aziridination Mediated by Arsonium Ylides: Preparation of trans-Pentafluorophenyl-Containing Aziridines

Abstract

Triphenylarsine catalyzes the formation of aziridines from tosyl imines and aromatic diazo compounds in a one-pot reaction. It is the first example of catalytic aziridination mediated by ­arsonium ylides. It gave aziridines in excellent diastereoselectivity with pentafluorophenyl diazomethane as the substrate. This catalytic reaction is complementary with the reaction mediated by sulfur ylides.

Key words

diazocompound - ylide - fluorine - aziridine - catalyze

References

• 1a van Santen RA. Kuipers HPC. Adv. Catal.  1987,  35:  265 
• 1b Zwanenburg B. ten Holte P. In Stereoselective Heterocyclic Synthesis III   Vol. 216:  Metz P. Topics in Current Chemistry, Springer; Berlin: 2001.  p.93-124  
• 2 Müller P. Fruit C. Chem. Rev.  2003,  103:  2905 
• 3 Aggarwal VK. Alonson E. Fang G. Ferrara M. Hynd G. Porcelloni M. Angew. Chem., Int. Ed. Engl.  1994,  33:  599 
• 4a Aggarwal VK. Patel M. Studley J. Chem. Commun.  2002,  1514 
• (b) Tewari RS. Chaturvedi SC. Tetrahedron Lett.  1977,  43:  3843 
• For reviews on arsonium ylides:
• (c) Lloyd D. Gosney I. Ormiston RA. Chem. Soc. Rev.  1987,  16:  45 
• (d) Huang Y. Sheng Y. Adv. Organomet. Chem.  1982,  20:  113 
• (e) Johnson AW. Ylide Chemistry   Academic Press; New York: 1966. 
• 5 Zhu SF. Liao YX. Zhu SZ. Org. Lett.  2004,  6:  377 
• 6 Dudman CC. Reese CB. Synthesis  1982,  419 
• 7a Ramachandran PV. In Asymmetric Fluoroorganic Chemistry: Synthesis Applications and Future Directions, ACS Symposium Series 746   American Chemical Society; Washington DC: 2000. 
• 7b Ojima I. McCarthy JR. Welch JT. In Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639   American Chemical Society; Washington DC: 1996. 
• 7c Kukhar’ VP. Soloshonok VA. In Fluorine-containing Amino Acids: Synthesis and Properties   Wiley; New York: 1995. 
• 7d Welch JT. In Selective Fluorination in Organic and Bioorganic Chemistry, ACS Symposium Series 456   American Chemical Society; Washington DC: 1991. 
• 7e Welch JT. Eswarakrishnan S. In Fluorine in Bioorganic Chemistry   Wiley & Sons; New York: 1991. 
• 8a Strehmel B. Sarker AM. Malpert JH. Strehmel V. Seifert H. Neckers DC. J. Am. Chem. Soc.  1999,  121:  1226 
• 8b Brooke GM. Mawson SD. J. Fluorine Chem.  1990,  50:  111 
• 8c Feast WJ. Lovenich PW. Puschmann H. Taliani C. Chem. Commun.  2001,  505 
• 8d Yu L. Bao Z. Adv. Mater.  1994,  6:  156 
• 8e Coates GW. Dunn AR. Henling LM. Ziller JW. Lobkovskey EB. Grubbs RH. J. Am. Chem. Soc.  1998,  120:  3641 
• 8f Krebs FC. Jensen T. J. Fluorine Chem.  2003,  120:  77