Beilstein J. Org. Chem.2011,7, 1327–1333, doi:10.3762/bjoc.7.156
), two diols 8 and 9, available from previous work, were converted to the biscarbamates 10 and 11. The metallation of O-benzylcarbamates has been studied extensively by Hoppe [1][24][25][26], and the deprotonation of 10 was achieved with sec-BuLi in ether and the addition of acetone, returning 12 as a
PDF
Graphical Abstract
Scheme 1:
Desymmetrising metallation for the enantioselective synthesis of atropisomers.
Beilstein J. Org. Chem.2011,7, 246–253, doi:10.3762/bjoc.7.33
Benan Kilbas Metin Balci Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey Department of Chemistry, Faculty of Sciences, Düzce University, 81620 Düzce, Turkey 10.3762/bjoc.7.33 Abstract Oxazolidinones can be synthesized starting from cyclic biscarbamates via a
nucleophile is not necessary to form oxazolidinones. The metal is probably bonded to the allylic system from the same face as the nucleophile.
Keywords: bicyclic endoperoxides; biscarbamates; oxazolidinone; Pd-catalyzed allylic reaction; singlet oxygen; Introduction
Palladium-catalyzed carbon–carbon bond
diacetates 15 and 18b. The isomeric diols 14 and 18a were treated with 2 equiv of toluenesulfonyl isocyanate as described above to give the corresponding biscarbamates 16 and 19. Treatment of 16 and 19 with the palladium catalyst (as described above) resulted in the formation of oxazolidinone derivatives 17
PDF
Graphical Abstract
Scheme 1:
General route to oxazolidinones via a palladium-catalyzed reaction.