Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study
Yükleniyor...
Dosyalar
Tarih
2011
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Beilstein-Institut
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
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.
Açıklama
WOS: 000287686300001
PubMed: 21448246
PubMed: 21448246
Anahtar Kelimeler
bicyclic endoperoxides, biscarbamates, oxazolidinone, Pd-catalyzed allylic reaction, singlet oxygen
Kaynak
Beilstein Journal Of Organic Chemistry
WoS Q Değeri
Q2
Scopus Q Değeri
Q2
Cilt
7
