Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York A Novel Synthesis of N-But-3-enyl-α- and β-Amino Acids T. T. Van Nguyen, Robert T. C. Brownlee, Andrew B. Hughes*Department of Chemistry, La Trobe University, Victoria 3086, AustraliaFax: +61(3)94791399; e-Mail: a.hughes@latrobe.edu.au; Recommend Article Abstract Buy Article All articles of this category Abstract N-But-3-enyl-α- and β-amino acids can be prepared by cleaving 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones in the presence of allylsilanes and boron trifluoride etherate at room temperature in good to excellent yields. Key words 1,3-oxazolidin-5-ones - 1,3-oxazinan-6-ones - amino acids - allylations - Lewis acids Full Text References References 1 Aurelio L. Brownlee RTC. Hughes AB. Chem. Rev. 2004, 104: 5823 2 Cole DC. Tetrahedron 1994, 50: 9517 3 Aurelio L. Brownlee RTC. Hughes AB. Sleebs BE. Aust. J. Chem. 2000, 53: 425 4 Hughes AB. Sleebs BE. Helv. Chim. Acta 2006, 89: 2611 5 Hughes AB. Sleebs BE. Synth. Commun. 2009, 39: 48 6 Govender T. Arvidsson PI. Tetrahedron Lett. 2006, 47: 1691 7 Sleebs BE. Synthesis of Beta Amino Acid Derivatives, Ph.D. Thesis La Trobe University; Australia: 2004. p.56-58 8 Aurelio L. Box JS. Brownlee RTC. Hughes AB. Sleebs MM. J. Org. Chem. 2003, 68: 2652 9 Ye T. McKervey MA. Chem. Rev. 1994, 94: 1091 10 Kirmse W. Eur. J. Org. Chem. 2002, 2193 11 Kantharaju BSP. Babu VVS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2005, 44: 2611 12 Arndt F. Eistert B. Partale W. Ber. Dtsch. Chem. Ges. 1927, 60: 1364 13 Gill GB. In The Wolff Rearrangement in Comprehensive Organic Synthesis Pergamon; New York: 1991. p.887 14 Patil BS. Vasanthakumar GR. Babu VVS. Synth. Commun. 2003, 33: 3089 15 Baldwin SE. Aube J. Tetrahedron Lett. 1987, 28: 179 16 Plucinska K. Liberek B. Tetrahedron 1987, 43: 179 17 Ellmerer-Mueller EP. Broessner D. Maslouh N. Tako A. Helv. Chim. Acta 1998, 81: 59 18 Leggio A. Liguori A. Procopio A. Sindona G. J. Chem. Soc., Perkin Trans. 1 1997, 1969 19 Muller A. Vogt C. Sewald N. Synthesis 1998, 837 20 Hughes AB. Sleebs BE. Helv. Chim. Acta 2006, 89: 2611 21 Proctor LD. Warr AJ. Org. Process Res. Dev. 2002, 6: 884 22 Pizey JS. Synthetic Reagents Vol. 2: Wiley; New York: 1974. p.65 23 Cesar J. Dolenc MS. Tetrahedron Lett. 2001, 42: 7099 24 Stromnova TA. Paschenko DV. Boganova LI. Daineko VM. Katser SB. Churakov AV. Kuz’mina LG. Howard JAK. Inorg. Chim. Acta 2003, 350: 283 25 Seebach D. Overhand M. Kuhnle FNM. Martinoti B. Oberer L. Hommel V. Widmer H. Helv. Chim. Acta 1996, 79: 913 26 Pillot JP. Dunogues J. Calas R. Tetrahedron Lett. 1976, 1871 27 Perrin DD. Armarego WLF. In Purification Of Laboratory Chemicals Pergamon; Oxford: 1988. 28 Aurelio L. Studies Towards the Natural Antifungal Cyclodepsipeptide Petriellin A, Methodology Concerning N-Methyl Amino Acids, Ph.D. Thesis La Trobe University; Australia: 2004. p.115-116 29 Podlech J. Seebach D. Helv. Chim. Acta 1995, 78: 1238 30 Gordon EM. Godfrey JD. Delaney NG. Asaad MM. Von Langen D. Cushman DW. J. Med. Chem. 1988, 31: 2199 31 Plucinska K. Liberek B. Tetrahedron 1987, 43: 3509