@article{KruegerLinker2021,
  author    = {Kr{\"u}ger, Tobias and Linker, Torsten},
  title     = {Synthesis of gamma-spirolactams by Birch reduction of arenes},
  series = {European journal of organic chemistry},
  volume    = {2021},
  journal   = {European journal of organic chemistry},
  number    = {10},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1099-0690},
  doi       = {10.1002/ejoc.202100056},
  pages     = {1585 -- 1591},
  year      = {2021},
  abstract  = {A convenient method for the synthesis of gamma-spirolactams in only three steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of chloroacetonitrile affords nitriles in moderate to good yields. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and anthroic acid. Subsequent catalytic hydrogenation proceeds smoothly with PtO2 or Raney Ni as catalysts and lactams are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation at different pressures, affording products with 0, 1, or 2 double bonds. Overall, more than 15 new gamma-spirolactams have been synthesized in analytically pure form.},
  language  = {en}
}
@article{KruegerBramborgKellingetal.2021,
  author    = {Kr{\"u}ger, Tobias and Bramborg, Andrea and Kelling, Alexandra and Sperlich, Eric and Linker, Torsten},
  title     = {Birch Reduction of Arenes as an Easy Entry to γ-Spirolactones},
  series = {European journal of organic chemistry},
  volume    = {2021},
  journal   = {European journal of organic chemistry},
  number    = {46},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.202101018},
  pages     = {6383 -- 6391},
  year      = {2021},
  abstract  = {A convenient method for the synthesis of γ-spirolactones in only 2-3 steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of ethylene oxide affords hydroxy acids, which undergo direct lactonization during work-up. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and dicarboxylic acids. Subsequent hydrogenation proceeds smoothly with Pd/C as catalyst and saturated γ-spirolactones are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation with Raney nickel or Wilkinson's catalyst to obtain products with 1 double bond. Overall, more than 30 new γ-spirolactones have been synthesized in analytically pure form.},
  language  = {en}
}
@article{BramborgLinker2012,
  author    = {Bramborg, Andrea and Linker, Torsten},
  title     = {Regioselective synthesis of alkylarenes by two-step ipso-substitution of aromatic dicarboxylic acids},
  series = {European journal of organic chemistry},
  journal   = {European journal of organic chemistry},
  number    = {28},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.201200823},
  pages     = {5552 -- 5563},
  year      = {2012},
  abstract  = {A strategy for the regioselective alkylation of arenes was developed, starting from commercially available and inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid. The method entails a formal ipso-substitution of the carboxylate groups by a sequence of reductive alkylation under Birch conditions and subsequent acid-mediated rearomatization with loss of carbon monoxide and carbon dioxide. More than 20 different arenes with various side-chains were synthesized. With naphthalene-1,4-dicarboxylic acid as starting material, we were able to control the degree of alkylation by choosing the appropriate electrophile in the Birch reduction. Thus, bisalkylated naphthalenes and naphthoic acids became available chemoselectively. All reactions afforded a single regioisomer exclusively in high yields. Overall, aromatic dicarboxylic acids are suitable substrates for a two-step ipso-substitution that allows the selective synthesis of alkylated benzenes and naphthalenes.},
  language  = {en}
}