@article{MaticSchlaad2018,
  author    = {Matic, Aleksandar and Schlaad, Helmut},
  title     = {Thiol-ene photofunctionalization of 1,4-polymyrcene},
  series = {Polymer international},
  volume    = {67},
  journal   = {Polymer international},
  number    = {5},
  publisher = {Wiley},
  address   = {Hoboken},
  issn      = {0959-8103},
  doi       = {10.1002/pi.5534},
  pages     = {500 -- 505},
  year      = {2018},
  abstract  = {1,4-Polymyrcene was synthesized by anionic polymerization of -myrcene and was subjected to photochemical functionalization with various thiols (i.e. methyl thioglycolate, methyl 3-mercaptopropionate, butyl 3-mercaptopropionate, ethyl 2-mercaptopropionate and 2-methyl-2-propanethiol) using benzophenone/UV light as the radical source. The yield of thiol addition to the trisubstituted double bonds of 1,4-polymyrcene decreased in the order 1 degrees thiol (ca 95\%) > 2 degrees thiol (ca 80\%) > 3 degrees thiol (<5\%), due to the reversibility of the thiol-ene reaction. Remarkably, thiol addition to the side-chain double bonds was 8 - 10 times (1 degrees thiol) or 24 times (2 degrees thiol) faster than to the main-chain double bonds, which can be explained by the different accessibility of the double bonds and steric hindrance. Despite the use of a 10-fold excess of thiol with respect to myrcene units, the thiol-ene addition was accompanied by chain coupling reactions, which in the extreme case of 3 degrees thiol (or in the absence of thiol) resulted in the formation of insoluble crosslinked material. As an example, a methyl-thioglycolate-functionalized 1,4-polymyrcene was saponified/crosslinked to give submicron polyelectrolyte particles in dilute alkaline solution. (c) 2018 Society of Chemical Industry},
  language  = {en}
}
@article{BauchBoettcherBornscheueretal.2016,
  author    = {Bauch, Marcel and B{\"o}ttcher, Dominique and Bornscheuer, Uwe T. and Linker, Torsten},
  title     = {Enzymatic Cleavage of Aryl Acetates},
  series = {ChemCatChem : heterogeneous \& homogeneous \& bio- \& nano-catalysis ; a journal of ChemPubSoc Europe},
  volume    = {8},
  journal   = {ChemCatChem : heterogeneous \& homogeneous \& bio- \& nano-catalysis ; a journal of ChemPubSoc Europe},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  organization    = {HESS Collaboration},
  issn      = {1867-3880},
  doi       = {10.1002/cctc.201600678},
  pages     = {2853 -- 2857},
  year      = {2016},
  abstract  = {Seven enzymes have been screened for the cleavage of aryl acetates. Phenyl and naphthyl acetates react with lipases and esterases, whereas the sterically demanding anthracene acetate gave a conversion only with porcine liver esterase and esterase 2 from Bacillus subtilis (BS2). These two enzymes have been employed on a preparative (0.5 mmol) scale and afforded cleavage products in 91 and 94\% yields, even for anthracene acetate. Thus, this method is superior to chemical cleavage with catalytic amounts of sodium methoxide (Zemplen conditions), which gave only low conversions. Finally, regioselectivity has been achieved with an anthracene bisacetate, in which an ethyl group controls the cleavage of the first acetate. This indicates that steric interactions play a crucial role in the enzymatic cleavage of aryl acetates, which might be interesting for future applications or the development of enzyme inhibitors.},
  language  = {en}
}
@article{FudickarVomdranLinker2006,
  author    = {Fudickar, Werner and Vomdran, Katja and Linker, Torsten},
  title     = {Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes},
  series = {Tetrahedron},
  volume    = {62},
  journal   = {Tetrahedron},
  number    = {46},
  publisher = {Elsevier},
  address   = {Oxford},
  issn      = {0040-4020},
  doi       = {10.1016/j.tet.2006.07.104},
  pages     = {10639 -- 10646},
  year      = {2006},
  abstract  = {The photooxygenation of homochiral cyclohexene ketals, which are easily available from 2-cyclohexenone and L-tartrates, affords hydroperoxides and after reduction the corresponding allylic alcohols in good yields and high regioselectivities. This can be rationalized by electronic repulsions in a perepoxide intermediate and provides evidence for unfavorable 1,3 diaxial interactions with a dioxolane oxygen atom. Only low stereoselectivities were observed, due to the flexibility of the cyclohexene ring. However, the diastereomers could be separated and after cleavage of the auxiliary, 4-hydroxy-2-cyclohexen-1-one was isolated in enantiomerically pure form, which can serve as a building block for natural product synthesis.},
  language  = {en}
}