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(Enantio)selective Hydrogen Autotransfer: Ruthenium‐Catalyzed Synthesis of Oxazolidin‐2‐ones from Urea and Diols
Author(s) -
PeñaLópez Miguel,
Neumann Helfried,
Beller Matthias
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600698
Subject(s) - ruthenium , regioselectivity , chemistry , amination , atom economy , catalysis , urea , vicinal , combinatorial chemistry , ligand (biochemistry) , domino , hydrogen bond , alcohol , nucleophilic substitution , organic chemistry , molecule , biochemistry , receptor
A novel strategy for the synthesis of oxazolidin‐2‐ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C−O and C−N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. While this transformation is already highly chemo‐ and regioselective, we also developed the first asymmetric version of this method using ( R )‐(+)‐MeO‐BIPHEP as the chiral ligand.