[2+2] Cycloaddition Reactions of Exo-Glycal Derivatives

Session: 
PS2 Poster session 2 Even numbers
Code: 
P102
Location (hall): 
Foyer
Start/end time: 
Tuesday, July 2, 2019 - 15:45 to 17:15
László
Juhász

László Juhász1, János József1, Tünde Zita Illyés1, Katalin E. Kövér2, László Somsák1

1Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary, 2Department of Inorganic and Analitycal Chemistry, University of Debrecen, Debrecen, 

Glycals are carbohydrate derivatives possessing double bond on the C-1 carbon. While in endo-glycals the π-bond is a part of the ring, in exo-glycals (1) a methylene or substituted methylene group is attached to the C-1 centre [1-3].

While there are several literature examples for cycloaddition reactions of endo-glycals with isocyanates (2) and dichloroketene (3) to give β- and γ-lactams as well as cyclobutanone derivatives [4, 5], only a few examples of cycloadditions of exo-glycals are published [6-8], and especially the above-mentioned transformations are unknown.

The goal of our research was to study the [2+2] cycloaddition reactions of exo-glycal (1) derivatives with chlorosulfonyl-isocyanate (2) and dichloroketene (3) to obtain new spiro β- and γ-lactames (4, 5) and spiro cyclobutanones (6) (See. Figure 1.).

Figure 1.

Acknowlegements

The research was supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008, and by the National Research, Development and Innovation Office under the project FK128766.

References: 
  1. Tolstikov, A. G.; Tolstikov, G. A. Usp. Khim. 1993, 62, 621.
  2. Priebe, W.; Grynkiewicz, G. In Glycoscience: Chemistry and Chemical Biology. Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer: Berlin, Heidelberg, 2001; Vol. I, pp. 749.
  3. Ferrier, R. J.; Hoberg, J. O. Adv. Carbohydr. Chem. Bi. 2003, 58, 55.
  4. Chmielewski, M.; Kaluza, Z.; Furman, B.; Chem. Commun. 1996, 2689. 
  5. Linker, T.; Umbreen, S.; Chem. Eur. J., 2015, 21, 1.
  6. Li, X.; Takahashi, H.; Ohtake, H.; Ikegami, S. Tetrahedron Lett. 2004, 45, 4123.
  7. Li, X.; Takahashi, H.; Ohtake, H.; Ikegami, S. Heterocycles, 2003, 59, 547.
  8. Massen, Z. S. Sarli, V. C.; Coutouli-Argyropoulou, E.; Gallos, J. K.; Carbohydr. Res. 2011, 346, 230.
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