Straightforward Synthesis of Novel Enantiopure α-Trifluoromethylated Azetidine 2-Carboxylic Acid and Homoserines
作者： Nathalie Lensen , Joyce Marais , Thierry Brigaud
DOI: 10.1021/OL503448W
关键词:
摘要: The straightforward syntheses of enantiopure (2R)-2-trifluoromethyl-2-carboxyazetidine and (R)- (S)-trifluoromethylhomoserines are reported. key step is a Strecker-type reaction on common chiral CF3-containing bicyclic oxazolidine intermediate obtained by condensation (R)-phenylglycinol ethyl-4,4,4-trifluoroacetoacetate (ETFAA).
acs.org
core.ac.uk
sci-hub.se 参考文章(51)
Current fluoroorganic chemistry : new synthetic directions, technologies, materials, and biological applications American Chemical Society. ,(2007) , 10.1021/BK-2007-0949
Iwao Ojima, Fluorine in medicinal chemistry and chemical biology Wiley. ,(2009) , 10.1002/9781444312096
Asta Žukauskaitė, Alessandro Moretto, Cristina Peggion, Marta De Zotti, Algirdas Šačkus, Fernando Formaggio, Norbert De Kimpe, Sven Mangelinckx, Synthesis and Conformational Study of Model Peptides Containing N-Substituted 3-Aminoazetidine-3-carboxylic Acids European Journal of Organic Chemistry. ,vol. 2014, pp. 2312- 2321 ,(2014) , 10.1002/EJOC.201301741
Mark R. Faust, Georg Höfner, Jörg Pabel, Klaus T. Wanner, Azetidine derivatives as novel γ-aminobutyric acid uptake inhibitors: Synthesis, biological evaluation, and structure–activity relationship European Journal of Medicinal Chemistry. ,vol. 45, pp. 2453- 2466 ,(2010) , 10.1016/J.EJMECH.2010.02.029
Xiao-Long Qiu, Feng-Ling Qing, Recent Advances in the Synthesis of Fluorinated Amino Acids European Journal of Organic Chemistry. ,vol. 2011, pp. 3261- 3278 ,(2011) , 10.1002/EJOC.201100032
Florent Huguenot, Thierry Brigaud, Concise Synthesis of Enantiopure α-Trifluoromethyl Alanines, Diamines, and Amino Alcohols via the Strecker-type Reaction Journal of Organic Chemistry. ,vol. 71, pp. 7075- 7078 ,(2006) , 10.1021/JO0607717
Joel Slade, Joginder Bajwa, Hui Liu, David Parker, James Vivelo, Guang-Pei Chen, John Calienni, Edwin Villhauer, Kapa Prasad, Oljan Repič, Thomas J. Blacklock, A Concise Synthesis of a Novel Insulin-Like Growth Factor I Receptor (IGF-IR) Inhibitor† Organic Process Research & Development. ,vol. 11, pp. 825- 835 ,(2007) , 10.1021/OP700052U
Vivian Asante, Jérémie Mortier, Gerhard Wolber, Beate Koksch, Impact of fluorination on proteolytic stability of peptides: a case study with α-chymotrypsin and pepsin Amino Acids. ,vol. 46, pp. 2733- 2744 ,(2014) , 10.1007/S00726-014-1819-7
Beate Koksch, Norbert Sewald, Hans-Jörg Hofmann, Klaus Burger, Hans-Dieter Jakubke, Proteolytically stable peptides by incorporation of α‐Tfm amino acids Journal of Peptide Science. ,vol. 3, pp. 157- 167 ,(1997) , 10.1002/(SICI)1099-1387(199705)3:3<157::AID-PSC94>3.0.CO;2-W
José Luis Baeza, Guillermo Gerona-Navarro, Jesús Pérez de Vega, M. Teresa García-López, Rosario González-Muñiz, Mercedes Martín-Martínez, Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction Journal of Organic Chemistry. ,vol. 73, pp. 1704- 1715 ,(2008) , 10.1021/JO701746W