Synthesis of Bicyclic Adduct through Regioselective Baeyer-Villager oxidation


Synthesis of Bicyclic Adduct through Regioselective Baeyer-Villager oxidation


Bello Y. Makama* and Wahidullah Azizi

Division of Mathematics, Sciences & Technology, American University of Afghanistan, Darul-Amman, Kabul, Afghanistan


American journal of chemical research-2d-code

Baeyer-Villager oxidation reaction has become accepted as a right approach in the ring expansions for the preparation of both bicyclic and tricyclic lacotnes; however, successful application of the regioselective Bayer-Villager oxidation protocol to the synthesis of particularly congested scaffolds remains distinctly tricky. Herein the Baeyer–Villiger oxidation of Bicyclo[3.2.0]hept-3-ene-6-one is studied with oxygen insertion leading to the functionalized oxabicyclic adduct with complete regioselectivity.


Keywords: bicyclic adduct, regioselectivity, Bayer Villager oxidation, synthesis

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How to cite this article:
Bello Y. Makama and Wahidullah Azizi. Synthesis of Bicyclic Adduct through Regioselective Baeyer-Villager oxidation. American Journal of Chemical Research, 2018, 2:9. DOI: 10.28933/ajcr-2018-11-1208


References:
1. Makama, B. Y. (2010). Ring Expansions using Baeyer-Villiger oxidation: An efficient strategy for the construction of substituted AB-ring systems. Org. Com-mun., 3(4), 84-91.
2. Makama, B. Y. (2011). Functionalization of AB-ring systems: An efficient pro-tocol towards Tricyclic Lactones. International Journal of Natural and Applied Science., 7(3), 281-285.
3. Butkus, E., & Stoncius, S. (2001, 8). Stereoselective Baeyer-Villiger oxidation of some bridged bicyclic diketones. Journal of the Chemical Society Perkin Transaction, 16(16), 1885-1888.
4. Brink, G. J., Arends, I. W., & Sheldon, R. A. (2004). The Baeyer-Villiger Reac-tion: New developments toward Greener Procedures. Chem. Rev., 104(9), 4105-4124.
5. Grieco, P. A. (1972). Cyclopentenones. Efficient synthesis of cis-jasome. J. Org. Chem, 37(14), 2363-2364.
6. Grieco, P. A., & Hiroi, K. (1972). α-Hydroxymethylation of γ- and δ-lactones: a new synthesis of α-methylene-γ-butyrolactones. Journal of the Chemical Socie-ty, Chemical Communications., 0, 1317-1318.