Dimethyl carbonate in the regio- and stereocontrolled opening of three-membered heterocyclic rings

In an attempt to replace harmful or carcinogenic solvents (such as dichloromethane, acetone, etc.) with non-harmful and greener ones, the possibility of performing four already developed ring-opening methodologies in a more eco-friendly media, such as DMC, has been investigated. The results show that the usual employed solvents (CH2Cl2, Et2O, CH3CN, etc.) can be easily replaced by DMC: not only the stereo- and regioselectivity is conserved, but also the work-up is simplified to a filtration, therefore reducing considerably the amount of solvents employed in the processes, and all the reactions are performed at room temperature, even the ones previously reported at low temperatures.

[1]  G. Righi,et al.  A New, simple, and mild azidolysis of vinylepoxides , 2011 .

[2]  M. Kiefel,et al.  An efficient synthesis of selectively functionalized d-rhamnose derivatives , 2011 .

[3]  B. Zwanenburg,et al.  A convenient synthesis of aziridine‐2‐carboxylic esters , 2010 .

[4]  A. Perosa,et al.  Green chemistry metrics: a comparative evaluation of dimethyl carbonate, methyl iodide, dimethyl sulfate and methanol as methylating agents , 2008 .

[5]  G. Righi,et al.  Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir. , 2008, Bioorganic & medicinal chemistry.

[6]  G. Fabrizi,et al.  Dimethyl carbonate: an environmentally friendly solvent for hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3, MTO) catalytic oxidations , 2007 .

[7]  G. Righi,et al.  Highly efficient stereoselective synthesis of d-erythro-sphingosine and d-lyxo-phytosphingosine , 2006 .

[8]  C. Giuliano,et al.  An Easy Procedure for the Highly Regioselective Conversion of Epoxides to Halohydrins , 2006 .

[9]  G. Righi,et al.  Stereocontrolled Transformations of trans α,β‐Aziridine Aldehydes toward Different Amino Hydroxylated Structures , 2006 .

[10]  P. Moran,et al.  A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters : key intermediates for taxol side chain and phenylnorstatine , 2005 .

[11]  F. Bonino,et al.  Dimethyl carbonate in the supercages of NaY zeolite: the role of local fields in promoting methylation and carboxymethylation activity. , 2005, Angewandte Chemie.

[12]  L. Rossi,et al.  Dimethyl carbonate as an ambident electrophile. , 2005, The Journal of organic chemistry.

[13]  S. Memoli,et al.  Synthesis of methylethers by reaction of alcohols with dimethylcarbonate , 2004 .

[14]  S. Kim,et al.  Regio- and stereoselective ring opening of vinyl epoxides with MgBr2 , 2004 .

[15]  G. Righi,et al.  New stereoselective synthesis of the peptidic aminopeptidase inhibitors bestatin, phebestin and probestin , 2003 .

[16]  A. Perosa,et al.  Green organic syntheses: organic carbonates as methylating agents. , 2002, Chemical record.

[17]  G. Righi,et al.  Stereo- and regioselective ring opening of alkenyl aziridines with metal halides , 2002 .

[18]  Pietro Tundo,et al.  The chemistry of dimethyl carbonate. , 2002, Accounts of chemical research.

[19]  G. Righi,et al.  A Study on the “Non-Chelation Controlled” Organometallic Addition totrans α,β-Epoxy Aldehydes − A Straightforward Stereoselective Synthesis of the Abbot Amino Dihydroxyethylene Dipeptide Isoster , 2002 .

[20]  P. Tundo.  New developments in dimethyl carbonate chemistry , 2001 .

[21]  M. Selva,et al.  Dimethylcarbonate for eco-friendly methylation reactions. , 2001, Chemosphere.

[22]  G. Righi,et al.  Stereo- and regiocontrolled transformations of vinyloxiranes with metal halides , 2000 .

[23]  G. Righi,et al.  Chelation Control in the Ring Opening and Organometallic Addition of α,β‐Epoxy Aldehydes: a New Entry to Amino Dihydroxyethylene Dipeptide Isostere Subunits , 2000 .

[24]  G. Righi,et al.  Highly regioselective opening of optically active N-Boc-2,3-aziridino alcohol derivatives with metal halides , 1998 .

[25]  G. Righi,et al.  Metal halide-mediated opening of three membered rings: enantioselective synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and (3R)-3-aminodecanoic acid , 1997 .

[26]  Y. Ono,et al.  Dimethyl carbonate for environmentally benign reactions , 1996 .

[27]  G. Righi,et al.  Regioselective opening of 3-Substituted N-Ethoxycarbonyl aziridine-2-carboxylates with metal halides toward the preparation of α and β-amino acids , 1996 .

[28]  G. Righi,et al.  Stereoselective Preparation of Syn α-Hydroxy-β-amino Ester Units via Regioselective Opening of α,β-Epoxy Esters: Enantioselective Synthesis of Taxol C-13 Side Chain and Cyclohexylnorstatine , 1996 .

[29]  G. Righi,et al.  A simple route to syn α-Amino-β-Hydroxy esters by C-2 regioselective opening of a, β-Epoxy esters with metal halides , 1995 .

[30]  F. Rivetti,et al.  OXIDATIVE CARBONYLATION OF METHANOL TO DIMETHYL CARBONATE (DMC) : A NEW CATALYTIC SYSTEM , 1995 .

[31]  D. Tanner,et al.  Regioselective nucleophilic ring opening of 2,3-aziridino alcohols , 1992 .

[32]  G. Sotgiu,et al.  Regioselective Opening of Epoxy Alcohols: Mild Chemo- and Stereoselective Preparation of Iodohydrins and 1,2-Diols , 1991 .

[33]  Huan Liang,et al.  Asymmetric synthesis of (-)-dehydroclausenamide , 1990 .

[34]  K. Sharpless,et al.  Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization , 1987 .

[35]  K. Sharpless,et al.  High stereo- and regioselectivities in the transition metal catalyzed epoxidations of olefinic alcohols by tert-butyl hydroperoxide , 1973 .