Enantioselective synthesis of 2-oxazolidinones by ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones† †Electronic supplementary information (ESI) available. CCDC 1584965. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01869c

A highly enantioselective synthesis of optically active 4-substituted 2-oxazolidinones was described via ruthenium(ii)–NHC-catalysed asymmetric hydrogenation of 2-oxazolones.

[1]  F. Glorius,et al.  Hydrogenation of fluoroarenes: Direct access to all-cis-(multi)fluorinated cycloalkanes , 2017, Science.

[2]  Wei Li,et al.  Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins. , 2017, Journal of the American Chemical Society.

[3]  Wanbin Zhang,et al.  Asymmetric Hydrogenation of Nonaromatic Cyclic Substrates. , 2016, Chemical reviews.

[4]  Y. Shimizu,et al.  Diethylenetriamine-Mediated Direct Cleavage of Unactivated Carbamates and Ureas. , 2016, Organic letters.

[5]  C. Cho,et al.  Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (-)-Aurantioclavine. , 2016, Organic letters.

[6]  F. Glorius,et al.  N-Heterocyclic Carbenes in Asymmetric Hydrogenation , 2016 .

[7]  Yong‐Gui Zhou,et al.  Asymmetric Hydrogenation of Heteroarenes with Multiple Heteroatoms , 2016 .

[8]  Wei Li,et al.  Asymmetric Hydrogenation of Vinylthioethers: Access to Optically Active 1,5-Benzothiazepine Derivatives. , 2016, Angewandte Chemie.

[9]  Qingli Wang,et al.  New synthetic strategy for chiral 2-oxazolidinones derivatives via rhodium-catalyzed asymmetric hydrogenation , 2016 .

[10]  S. Nolan.  N-Heterocyclic carbenes , 2009, Beilstein journal of organic chemistry.

[11]  F. Glorius,et al.  An overview of N-heterocyclic carbenes , 2014, Nature.

[12]  Yanmei He,et al.  Advances in transition metal-catalyzed asymmetric hydrogenation of heteroaromatic compounds. , 2014, Topics in current chemistry.

[13]  F. Glorius,et al.  Asymmetric hydrogenation of thiophenes and benzothiophenes. , 2012, Journal of the American Chemical Society.

[14]  M. Andrus,et al.  Naphthyl-substituted bisoxazoline and pyridylbisoxazoline–copper(I) catalysts for asymmetric allylic oxidation , 2012 .

[15]  S. Nolan,et al.  N-heterocyclic carbene gold(I) and copper(I) complexes in C-H bond activation. , 2012, Accounts of chemical research.

[16]  Weiwei Jin,et al.  Brønsted acid activation strategy in transition-metal catalyzed asymmetric hydrogenation of N-unprotected imines, enamines, and N-heteroaromatic compounds. , 2012, Angewandte Chemie.

[17]  M. Shi,et al.  Chiral NHC–metal-based asymmetric catalysis , 2012 .

[18]  Yong‐Gui Zhou,et al.  Asymmetric hydrogenation of heteroarenes and arenes. , 2012, Chemical reviews.

[19]  Ka Hou Hoi,et al.  The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions. , 2012, Angewandte Chemie.

[20]  F. Glorius,et al.  Ruthenium NHC catalyzed highly asymmetric hydrogenation of benzofurans. , 2012, Angewandte Chemie.

[21]  F. Glorius,et al.  Ligand-controlled highly regioselective and asymmetric hydrogenation of quinoxalines catalyzed by ruthenium N-heterocyclic carbene complexes. , 2011, Angewandte Chemie.

[22]  Shou‐Fei Zhu,et al.  Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. , 2011, Chemical reviews.

[23]  S. Nolan,et al.  N-heterocyclic carbenes in late transition metal catalysis. , 2009, Chemical reviews.

[24]  R. Kuwano.  CATALYTIC ASYMMETRIC HYDROGENATION OF 5-MEMBERED HETEROAROMATICS , 2008 .

[25]  F. Hahn,et al.  Heterocyclic carbenes: synthesis and coordination chemistry. , 2008, Angewandte Chemie.

[26]  Yong‐Gui Zhou.  Asymmetric hydrogenation of heteroaromatic compounds. , 2007, Accounts of chemical research.

[27]  I. Dragutan,et al.  NHC–Ru complexes—Friendly catalytic tools for manifold chemical transformations , 2007 .

[28]  S. Bellemin‐Laponnaz,et al.  Mixed oxazoline-carbenes as stereodirecting ligands for asymmetric catalysis , 2007 .

[29]  F. Glorius.  N-Heterocyclic Carbenes in Transition Metal Catalysis , 2007 .

[30]  S. Nolan.  N-Heterocyclic Carbenes in Synthesis: NOLAN:N-HETEROCYCL. CARB. O-BK , 2006 .

[31]  S. Bellemin‐Laponnaz,et al.  Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis. , 2004, Chemical Society reviews.

[32]  Xumu Zhang,et al.  New chiral phosphorus ligands for enantioselective hydrogenation. , 2003, Chemical reviews.

[33]  K. Burgess,et al.  Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis , 2003 .

[34]  F. Rutjes,et al.  An Efficient Synthesis of 1‐Naphthylbis(oxazoline) and Exploration of the Scope in Asymmetric Catalysis , 2003 .

[35]  W. Herrmann.  N-heterocyclic carbenes: a new concept in organometallic catalysis. , 2002, Angewandte Chemie.

[36]  Macgregor Ea.  Zolmitriptan clinical studies. , 1998 .

[37]  J. M. Takacs,et al.  Preparation of Chiral Oxazolidin-2-ones and Vicinal Amino Alcohols. , 1998, The Journal of organic chemistry.

[38]  D. Ager,et al.  1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. , 1996, Chemical reviews.

[39]  Jacqueline Seyden-Penne,et al.  Chiral Auxiliaries and Ligands in Asymmetric Synthesis , 1995 .

[40]  D. Evans,et al.  Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates , 1981 .