Synthesis of Chiral Cyclic Carbonates via Kinetic Resolution of Racemic Epoxides and Carbon Dioxide

The catalytic synthesis of cyclic carbonates using carbon dioxide as a C1-building block is a highly active area of research. Here, we review the catalytic production of enantiomerically enriched cyclic carbonates via kinetic resolution of racemic epoxides catalysed by metal-containing catalyst systems.

[1]  Elsje Alessandra Quadrelli,et al.  Carbon dioxide utilisation : closing the carbon cycle , 2015 .

[2]  S. Nguyen,et al.  Chiral (salen)Co(III) catalyst for the synthesis of cyclic carbonates. , 2004, Chemical communications.

[3]  Toshio Suzuki,et al.  Chiral C3 epoxides and halohydrins: Their preparation and synthetic application , 1998 .

[4]  Geonjoong Kim,et al.  Synthesis of chiral propylene carbonate via asymmetric ring opening of racemic propylene oxide by carbon dioxide on immobilized cobalt salen catalyst , 2012 .

[5]  Lili Jin,et al.  Chiral catalysts for the asymmetric cycloaddition of carbon dioxide with epoxides , 2008 .

[6]  Huanfeng Jiang,et al.  A chiral mixed metal-organic framework based on a Ni(saldpen) metalloligand: synthesis, characterization and catalytic performances. , 2013, Dalton transactions.

[7]  R. I. Kureshy,et al.  Asymmetric cycloaddition of CO2 and an epoxide using recyclable bifunctional polymeric Co(III) salen complexes under mild conditions , 2013 .

[8]  K. Nicolaou,et al.  Synthesis of C-2 taxol analogues , 1994 .

[9]  Michele Aresta,et al.  Enantioselective synthesis of organic carbonates promoted by Nb(IV) and Nb(V) catalysts , 2003 .

[10]  S. Sivaram,et al.  Organic Carbonates. , 1996, Chemical reviews.

[11]  A. Whitwood,et al.  Aluminum(salen) Complexes as Catalysts for the Kinetic Resolution of Terminal Epoxides via CO2 Coupling , 2015 .

[12]  Huanwang Jing,et al.  Chiral ionic liquids improved the asymmetric cycloaddition of CO2 to epoxides , 2009 .

[13]  A. Berkessel,et al.  Catalytic asymmetric addition of carbon dioxide to propylene oxide with unprecedented enantioselectivity. , 2006, Organic letters.

[14]  S. Ōae,et al.  Mild and selective reduction of sulfoxides in the mixture with other sulfinyl compounds with trifluoroacetic anhydride-hydrogen sulfide system. , 1977 .

[15]  Huanwang Jing,et al.  Chiral metal-containing ionic liquid: Synthesis and applications in the enantioselective cycloaddition of carbon dioxide to epoxides , 2011 .

[16]  Yizhan Luo,et al.  Role of the co-catalyst in the asymmetric coupling of racemic epoxides with CO2 using multichiral Co(III) complexes: product selectivity and enantioselectivity , 2012 .

[17]  Hui Wang,et al.  Asymmetric catalysis with CO2: direct synthesis of optically active propylene carbonate from racemic epoxides. , 2004, Journal of the American Chemical Society.

[18]  Geonjoong Kim,et al.  Efficient catalytic synthesis of optically active cyclic carbonates via coupling reaction of epoxides and carbon dioxide , 2007 .

[19]  Michele Aresta,et al.  Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. technological use of CO2. , 2014, Chemical reviews.

[20]  Geonjoong Kim,et al.  Asymmetric Ring Opening of Epoxides Catalyzed by Novel Heterobimetallic Schiff-Bases Containing Transition Metal Salts , 2008 .

[21]  Lili Jin,et al.  Quaternary onium tribromide catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides , 2007 .

[22]  Lili Jin,et al.  Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides , 2009 .

[23]  Huanwang Jing,et al.  Cinchona-Derived Quaternary Ammonium Salts-Improved Asymmetric Cycloaddition of CO2 to Epoxides , 2009 .

[24]  M. Aresta Carbon dioxide as chemical feedstock , 2010 .

[25]  Martina Peters,et al.  Chemical technologies for exploiting and recycling carbon dioxide into the value chain. , 2011, ChemSusChem.

[26]  L. Mussmann,et al.  Kinetic resolution of oxiranes by use of chiral Lewis acid catalysts , 1993 .

[27]  M. North,et al.  Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings , 2015 .

[28]  Huanwang Jing,et al.  Catalytic Asymmetric Cycloaddition of Carbon Dioxide and Propylene Oxide Using Novel Chiral Polymers of BINOL‐Salen‐ Cobalt(III) Salts , 2009 .

[29]  Tohru Yamada,et al.  Enantioselective Incorporation of Carbon Dioxide into Epoxides Catalyzed by Optically Active Cobalt(II) Complexes , 2007 .

[30]  Chiral Salen Complexes , 2012 .

[31]  Tohru Yamada,et al.  Enantioselective CO2 Fixation Catalyzed by Optically Active Cobalt Complexes. , 2004 .