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Collect. Czech. Chem. Commun. 1991, 56, 1365-1399
https://doi.org/10.1135/cccc19911365

Syntheses of β,γ-unsaturated α-amino acids

Libor Havlíček and Jan Hanuš

Institute of Nuclear Biology and Radiochemistry, Czechoslovak Academy of Sciences, 142 20 Prague 4

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  • Mu Wenbo, Zhou Lijun, Zou Yue, Wang Quanrui, Goeke Andreas: Irreversible Oxy‐2‐azonia‐Cope Rearrangements for the Synthesis of Functionalized Allyl α‐Amino Acid Derivatives. Eur J Org Chem 2014, 2014, 2379. <https://doi.org/10.1002/ejoc.201301818>
  • Liu Zhihua, Mehta Sukeshi J., Hruby Victor J.: Strategies for Asymmetric Synthesis of Amino Acids with γ,δ-Unsaturation. Organic Preparations and Procedures International 2012, 44, 222. <https://doi.org/10.1080/00304948.2012.676507>
  • Hang Jianfeng, Deng Li: Asymmetric synthesis of β,γ-unsaturated α-amino acids via efficient kinetic resolution with cinchona alkaloids. Bioorganic & Medicinal Chemistry Letters 2009, 19, 3856. <https://doi.org/10.1016/j.bmcl.2009.03.152>
  • Tiwari Shashi Kant, Gais Hans-Joachim, Lindenmaier Andreas, Babu Gadamsetti Surendra, Raabe Gerhard, Reddy Leleti Rajender, Köhler Franz, Günter Markus, Koep Stefan, Iska Vijaya Bhaskara Reddy: Functionalized Chiral Vinyl Aminosulfoxonium Salts:  Asymmetric Synthesis and Application to the Synthesis of Enantiopure Unsaturated Prolines, β,γ-Dehydro Amino Acids, and Cyclopentanoid Keto Aminosulfoxonium Ylides. J. Am. Chem. Soc. 2006, 128, 7360. <https://doi.org/10.1021/ja061152i>
  • Acherki Hassan, Alvarez-Ibarra Carlos, García-Navazo Gonzalo, Gómez-Sánchez Elena, Quiroga-Feijóo María L.: A new approach to vinyl glycine derivatives from (+)-(RS)-3-[(p-toluenesulfinyl)methyl]-1-oxa-4-azaspiro[4,5]decen-3-ene. Tetrahedron: Asymmetry 2004, 15, 3419. <https://doi.org/10.1016/j.tetasy.2004.09.010>
  • Sibi Mukund P., Rutherford Drew, Renhowe Paul A., Li Biqin: Investigations of a Nucleophilic Alaninol Synthon Derived from Serine. J. Am. Chem. Soc. 1999, 121, 7509. <https://doi.org/10.1021/ja9906249>
  • Woiwode Thomas F., Wandless Thomas J.: Efficient Synthesis of β,γ-Dehydrovaline. J. Org. Chem. 1999, 64, 7670. <https://doi.org/10.1021/jo990916s>
  • Aoyama Hiroshi, Mimura Norio, Ohno Hiroaki, Ishii Kiyonori, Toda Ayako, Tamamura Hirokazu, Otaka Akira, Fujii Nobutaka, Ibuka Toshiro: Regio- and stereoselectivity in reactions of 2,3-cis- and trans-3-alkyl-2-vinylaziridines with organocopper reagents: Importance of 2,3-cis-stereochemistry in controlling selectivity. Tetrahedron Letters 1997, 38, 7383. <https://doi.org/10.1016/S0040-4039(97)01726-7>
  • Humphrey John M., Chamberlin A. Richard: Chemical Synthesis of Natural Product Peptides:  Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides. Chem. Rev. 1997, 97, 2243. <https://doi.org/10.1021/cr950005s>
  • Petasis Nicos A., Zavialov Ilia A.: A New and Practical Synthesis of α-Amino Acids from Alkenyl Boronic Acids. J. Am. Chem. Soc. 1997, 119, 445. <https://doi.org/10.1021/ja963178n>
  • Meffre P., Le Goffic F.: β,γ-Alkynylα-amino acids: a synthetic challenge. Amino Acids 1996, 11, 313. <https://doi.org/10.1007/BF00807939>
  • Agami Claude, Bihan Dominique, Puchot-Kadouri Catherine: Reactions of glyoxal-derived iminium ions with unsaturated silyl and silyloxy reagents. Tetrahedron 1996, 52, 9079. <https://doi.org/10.1016/0040-4020(96)00450-4>
  • Meffre Patrick, Gauzy Laurence, Branquet Eric, Durand Philippe, Le Goffic François: Synthesis of optically active β,γ-alkynylglycine derivatives. Tetrahedron 1996, 52, 11215. <https://doi.org/10.1016/0040-4020(96)00630-8>
  • Griesbeck Axel G., Hirt Joachim: A photochemical route to vinylglycine and a vinylglycine dipeptide. Liebigs Ann./Recl. 1995, 1995, 1957. <https://doi.org/10.1002/jlac.1995199511275>
  • Duthaler Rudolf O.: Recent developments in the stereoselective synthesis of α-aminoacids. Tetrahedron 1994, 50, 1539. <https://doi.org/10.1016/S0040-4020(01)80840-1>
  • O'Donnell Martin J., Li Min, Bennett William D., Grote Todd: Synthesis of β,γ-unsaturated amino acid derivatives by alkyne carbometalation-palladium catalyzed coupling with 2-aza-π-allyl palladium complexes. Tetrahedron Letters 1994, 35, 9383. <https://doi.org/10.1016/S0040-4039(00)78548-0>
  • Ibuka Toshiro, Suzuki Keisuke, Habashita Hiromu, Otaka Akira, Tamamura Hirokazu, Mimura Norio, Miwa Yoshihisa, Taga Tooru, Fujii Nobutaka: (E)-stereoselective synthesis of vinylglycines from (R)-serine via organocopper–BF3and related reagents. J. Chem. Soc., Chem. Commun. 1994, 2151. <https://doi.org/10.1039/C39940002151>
  • Ibuka Toshiro, Nakai Kazuo, Habashita Hiromu, Bessho Kiyoshi, Fujii Nobutaka, Chounan Yukiyasu, Yamamoto Yoshinori: Remarkable difference in reactivity of ordinary vinylcopper reagents and vinylzinc halide containing a copper salt towards γ-mesyloxy-α, β-enoates. Synthesis of homochiral 1,4-dienes. Tetrahedron 1993, 49, 9479. <https://doi.org/10.1016/S0040-4020(01)80217-9>
  • Guo Zhao-Xia, Schaeffer Marcel J., Taylor Richard J. K.: Synthesis of unsaturated α-amino acids using the Ramberg–Bäcklund reaction. J. Chem. Soc., Chem. Commun. 1993, 874. <https://doi.org/10.1039/C39930000874>
  • Bold Guido, Allmendinger Thomas, Herold Peter, Moesch Luzia, Schär Hans‐Peter, Duthaler Rudolf O.: Stereoselektive Synthese von (2S,6S)‐2,6‐Diaminoheptandisäure und von unsymmetrischen Derivaten der meso‐2,6‐Diaminoheptandisäure. Helvetica Chimica Acta 1992, 75, 865. <https://doi.org/10.1002/hlca.19920750321>
  • Zeiss Hans-Joachim: Enantioselective synthesis of L-phosphinothricin from L-methionine and L-glutamic acid via L-vinylglycine. Tetrahedron 1992, 48, 8263. <https://doi.org/10.1016/S0040-4020(01)80494-4>
  • HAVLICEK L., HANUS J.: ChemInform Abstract: Syntheses of β,γ‐Unsaturated α‐Amino Acids. ChemInform 1991, 22. <https://doi.org/10.1002/chin.199140301>