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@ARTICLE{Meyer:82180,
      author       = {Meyer, U. and Bisel, P. and Weckert, E. and Frahm, A. W.
                      and DESY},
      title        = {{B}icyclic glutamic acid derivatives},
      journal      = {Chirality},
      volume       = {18},
      issn         = {0899-0042},
      address      = {New York, NY [u.a.]},
      publisher    = {Wiley Interscience},
      reportid     = {PHPPUBDB-4925},
      pages        = {394},
      year         = {2006},
      abstract     = {For the second-generation asymmetric synthesis of the
                      trans-tris(homoglutamic) acids via Strecker reaction of
                      chiral ketimines, the cyanide addition as the key
                      stereodifferentiating step produces mixtures of
                      diastereomeric alpha-amino nitrile esters the composition of
                      which is independent of the reaction temperature and the
                      type of the solvent, respectively. The subsequent hydrolysis
                      is exclusively achieved with concentrated H(2)SO(4) yielding
                      diastereomeric mixtures of three secondary alpha-amino
                      alpha-carbamoyl-gamma-esters and two diastereomeric
                      cis-fused angular alpha-carbamoyl gamma-lactams as bicyclic
                      glutamic acid derivatives, gained from in situ stereomer
                      differentiating cyclisation of the secondary cis-alpha-amino
                      alpha-carbamoyl-gamma-esters. Separation was achieved by CC.
                      The pure secondary trans-alpha-amino
                      alpha-carbamoyl-gamma-esters cyclise on heating and
                      treatment with concentrated H(2)SO(4), respectively, to
                      diastereomeric cis-fused angular secondary alpha-amino
                      imides. Their hydrogenolysis led to the enantiomeric
                      cis-fused angular primary alpha-amino imides. The
                      configuration of all compounds was completely established by
                      NMR methods, CD-spectra, and by X-ray analyses of the
                      (alphaR,1R,5R)-1-carbamoyl-2-(1-phenylethyl)-2-azabicyclo[3.3.0]octan-3-one
                      and of the
                      trans-alphaS,1S,2R-2-ethoxycarbonylmethyl-1-(1-phenylethylamino)cyclopentanecarboxamide.},
      keywords     = {Amino Acids, Cyclic: chemistry / Amino Acids, Cyclic:
                      metabolism / Circular Dichroism / Crystallography, X-Ray /
                      Cyclization / Esters: chemistry / Glutamic Acid: analogs
                      $\&$ derivatives / Glutamic Acid: chemistry / Hot
                      Temperature / Hydrolysis / Models, Chemical / Molecular
                      Structure / Nuclear Magnetic Resonance, Biomolecular /
                      Solvents: chemistry / Stereoisomerism / Sulfuric Acids:
                      pharmacology / Amino Acids, Cyclic (NLM Chemicals) / Esters
                      (NLM Chemicals) / Solvents (NLM Chemicals) / Sulfuric Acids
                      (NLM Chemicals) / Glutamic Acid (NLM Chemicals) / sulfuric
                      acid (NLM Chemicals)},
      cin          = {HASYLAB},
      ddc          = {570},
      cid          = {$I:(DE-H253)HASYLAB_-2012_-20130307$},
      pnm          = {Facility (machine) DORIS/PETRA (POF1-DORIS-PETRA-20130405)},
      pid          = {G:(DE-H253)POF1-DORIS-PETRA-20130405},
      experiment   = {EXP:(DE-H253)DORISIII(machine)-20150101},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:16596563},
      UT           = {WOS:000237279100010},
      doi          = {10.1002/chir.20260},
      url          = {https://bib-pubdb1.desy.de/record/82180},
}