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.).
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.
- Tolstikov, A. G.; Tolstikov, G. A. Usp. Khim. 1993, 62, 621.
- 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.
- Ferrier, R. J.; Hoberg, J. O. Adv. Carbohydr. Chem. Bi. 2003, 58, 55.
- Chmielewski, M.; Kaluza, Z.; Furman, B.; Chem. Commun. 1996, 2689.
- Linker, T.; Umbreen, S.; Chem. Eur. J., 2015, 21, 1.
- Li, X.; Takahashi, H.; Ohtake, H.; Ikegami, S. Tetrahedron Lett. 2004, 45, 4123.
- Li, X.; Takahashi, H.; Ohtake, H.; Ikegami, S. Heterocycles, 2003, 59, 547.
- Massen, Z. S. Sarli, V. C.; Coutouli-Argyropoulou, E.; Gallos, J. K.; Carbohydr. Res. 2011, 346, 230.