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Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study
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10.3762:bjoc.7.33.pdf
Date
2011-2-24
Author
Kilbas, Benan
Balci, Metin
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Oxazolidinones can be synthesized starting from cyclic biscarbamates via a palladium-catalyzed reaction. To test the proposed mechanism of this reaction, first, bicyclonorcarene endoperoxides derived from cyano and carbomethoxy cycloheptatrienes were synthesized and converted into the corresponding diols. The reaction of diols with toluenesulfonyl isocyanate followed by a palladium catalyzed reaction furnished oxazolidinone derivatives in similar yields. It was shown that, if one face of the double bond is blocked by substituents such as H or CN, the reaction also takes place. On the basis of these results, it was assumed that an antiperiplanar orientation of the metal and nucleophile is not necessary to form oxazolidinones. The metal is probably bonded to the allylic system from the same face as the nucleophile.
Subject Keywords
Organic Chemistry
,
Bicyclic endoperoxides
,
Biscarbamates
,
Oxazolidinone
,
Pd-catalyzed allylic reaction
,
Singlet oxygen
URI
https://hdl.handle.net/11511/50975
Journal
Beilstein Journal of Organic Chemistry
DOI
https://doi.org/10.3762/bjoc.7.33
Collections
Department of Chemistry, Article
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B. Kilbas and M. Balci, “Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study,”
Beilstein Journal of Organic Chemistry
, pp. 246–253, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/50975.