Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine

Stephen P. Fletcher, Jordi Solà, Dean Holt, Robert A. Brown and Jonathan Clayden
Beilstein J. Org. Chem. 2011, 7, 1304–1309. https://doi.org/10.3762/bjoc.7.152

Cite the Following Article

Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
Stephen P. Fletcher, Jordi Solà, Dean Holt, Robert A. Brown and Jonathan Clayden
Beilstein J. Org. Chem. 2011, 7, 1304–1309. https://doi.org/10.3762/bjoc.7.152

How to Cite

Fletcher, S. P.; Solà, J.; Holt, D.; Brown, R. A.; Clayden, J. Beilstein J. Org. Chem. 2011, 7, 1304–1309. doi:10.3762/bjoc.7.152

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Wootten, M. M.; Le Bailly, B. A. F.; Tshepelevitsh, S.; Leito, I.; Clayden, J. Inducing a pH-dependent conformational response by competitive binding to Zn2+ of a series of chiral ligands of disparate basicity. Chemical science 2022, 13, 2258–2269. doi:10.1039/d1sc06812a
  • Cativiela, C.; Ordóñez, M.; Viveros-Ceballos, J. L. Stereoselective synthesis of acyclic α,α-disubstituted α-amino acids derivatives from amino acids templates. Tetrahedron 2020, 76, 130875. doi:10.1016/j.tet.2019.130875
  • Amer, M. M.; Abas, H.; Leonard, D. J.; Ward, J. W.; Clayden, J. Amino Acid-Derived trans- N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility. The Journal of organic chemistry 2019, 84, 7199–7206. doi:10.1021/acs.joc.9b00727
  • Ohtsuki, H.; Takashima, M.; Furuta, T.; Kawabata, T. Direct asymmetric synthesis of α-deuterated α-amino acid derivatives from the parent α-amino acids via memory of chirality. Tetrahedron Letters 2018, 59, 1188–1191. doi:10.1016/j.tetlet.2018.02.012
  • Diemer, V.; Maury, J.; Le Bailly, B. A. F.; Webb, S. J.; Clayden, J. Dibenzazepinyl ureas as dual NMR and CD probes of helical screw-sense preference in conformationally equilibrating dynamic foldamers. Chemical communications (Cambridge, England) 2017, 53, 10768–10771. doi:10.1039/c7cc06427f
  • Gratzer, K.; Diemer, V.; Clayden, J. Signal transduction in oligoamide foldamers by selective non-covalent binding of chiral phosphates at a urea binding site. Organic & biomolecular chemistry 2017, 15, 3585–3589. doi:10.1039/c7ob00660h
  • Tomsett, M.; Maffucci, I.; Le Bailly, B.; Byrne, L.; Bijvoets, S. M.; Lizio, M. G.; Raftery, J.; Butts, C. P.; Webb, S. J.; Contini, A.; Clayden, J. A tendril perversion in a helical oligomer: trapping and characterizing a mobile screw-sense reversal. Chemical science 2017, 8, 3007–3018. doi:10.1039/c6sc05474a
  • Kasamatsu, K.; Yoshimura, T.; Mándi, A.; Taniguchi, T.; Monde, K.; Furuta, T.; Kawabata, T. α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocyclobutenones with Tetrasubstituted Carbon. Organic letters 2017, 19, 352–355. doi:10.1021/acs.orglett.6b03533
  • Ueda, A.; Oba, M.; Izumi, Y.; Sueyoshi, Y.; Doi, M.; Demizu, Y.; Kurihara, M.; Tanaka, M. Helical structures of homo-chiral isotope-labeled α-aminoisobutyric acid peptides. Tetrahedron 2016, 72, 5864–5871. doi:10.1016/j.tet.2016.08.011
  • Le Bailly, B.; Clayden, J. Dynamic foldamer chemistry. Chemical communications (Cambridge, England) 2016, 52, 4852–4863. doi:10.1039/c6cc00788k
  • Le Bailly, B. A. F.; Byrne, L.; Clayden, J. Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond. Angewandte Chemie (International ed. in English) 2016, 55, 2132–2136. doi:10.1002/anie.201510605
  • Le Bailly, B. A. F.; Byrne, L.; Clayden, J. Refoldable Foldamers: Global Conformational Switching by Deletion or Insertion of a Single Hydrogen Bond. Angewandte Chemie 2016, 128, 2172–2176. doi:10.1002/ange.201510605
  • Maury, J.; Le Bailly, B. A. F.; Raftery, J.; Clayden, J. Conformational cooperativity between helical domains of differing geometry in oligoamide-oligourea foldamer chimeras. Chemical communications (Cambridge, England) 2015, 51, 11802–11805. doi:10.1039/c5cc02995c
  • Atkinson, R. C.; Fernández‐Nieto, F.; Mas Roselló, J.; Clayden, J. Pseudoephedrine‐Directed Asymmetric α‐Arylation of α‐Amino Acid Derivatives. Angewandte Chemie 2015, 127, 9089–9093. doi:10.1002/ange.201502569
  • Atkinson, R. C.; Fernández-Nieto, F.; Roselló, J. M.; Clayden, J. Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives. Angewandte Chemie (International ed. in English) 2015, 54, 8961–8965. doi:10.1002/anie.201502569
  • Brioche, J.; Pike, S. J.; Tshepelevitsh, S.; Leito, I.; Morris, G. A.; Webb, S. J.; Clayden, J. Conformational Switching of a Foldamer in a Multicomponent System by pH-Filtered Selection between Competing Noncovalent Interactions. Journal of the American Chemical Society 2015, 137, 6680–6691. doi:10.1021/jacs.5b03284
  • Gaudel-Siri, A.; Campolo, D.; Mondal, S.; Nechab, M.; Siri, D.; Bertrand, M. P. Theoretical Study To Explain How Chirality Is Stored and Evolves throughout the Radical Cascade Rearrangement of Enyne-allenes. The Journal of organic chemistry 2014, 79, 9086–9093. doi:10.1021/jo501450k
  • Le Bailly, B. A. F.; Clayden, J. Controlling the sign and magnitude of screw-sense preference from the C-terminus of an achiral helical foldamer. Chemical communications (Cambridge, England) 2014, 50, 7949–7952. doi:10.1039/c4cc03261f
  • Castagnolo, D.; Degennaro, L.; Luisi, R.; Clayden, J.
  • De Poli, M.; Clayden, J. Thionoglycine as a multifunctional spectroscopic reporter of screw-sense preference in helical foldamers. Organic & biomolecular chemistry 2013, 12, 836–843. doi:10.1039/c3ob42167h

Patents

  • JIAXING LU; RUINA LI; JIANQING ZHAO; HUAN WANG; LI HE; LIANG WU; XIAOMING XU; XUERU ZHAO. Method for synthesizing 2-(N-benzyl)methyl acetamido methylpropionate. CN 102586798 A, July 18, 2012.
Other Beilstein-Institut Open Science Activities