Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(12): 1991-1998
DOI: 10.1055/s-0028-1088072
DOI: 10.1055/s-0028-1088072
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Novel Synthesis of N-But-3-enyl-α- and β-Amino Acids
Further Information
Received
19 January 2009
Publication Date:
27 April 2009 (online)
Publication History
Publication Date:
27 April 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200912/lookinside/thumbnails/10.1055-s-0028-1088072-1.jpg)
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
- 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