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 2006(3): 455-460
DOI: 10.1055/s-2006-926273
DOI: 10.1055/s-2006-926273
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Applications of β-Aminoethanesulfonyl Azides
Further Information
Received
15 July 2005
Publication Date:
11 January 2006 (online)
Publication History
Publication Date:
11 January 2006 (online)
Abstract
A very efficient method for the synthesis of β-aminoethanesulfonyl azides is descibed. These aliphatic sulfonyl azides are accessible starting from a variety of protected amino acids, including those having functionalized side chains. Furthermore, these sulfonyl azides can be coupled to thio acids, and can be substituted with different aliphatic amines.
Key words
sulfonyl azide - sulfonyl chloride - amino acid - sulfonamides
- 1
Brouwer AJ.Monnee MCF.Liskamp RMJ. Synthesis 2000, 1579 -
2a
De Bont DBA.Dijkstra GDH.den Hartog JAJ.Liskamp RMJ. Bioorg. Med. Chem. Lett. 1996, 6: 3035 -
2b
De Bont DBA.Moree WJ.Liskamp RMJ. Bioorg. Med. Chem. 1996, 4: 667 -
2c
De Bont DBA.Sliedregt-Bol KM.Hofmeyer LJF.Liskamp RMJ. Bioorg. Med. Chem. 1999, 7: 1043 -
2d
Liskamp RMJ.Kruijtzer JAW. Mol. Diversity 2004, 8: 79 -
3a
Löwik DWPM.Mulders SJE.Cheng Y.Shao Y.Liskamp RMJ. Tetrahedron Lett. 1996, 37: 8253 -
3b
Löwik DWPM.Weingarten MD.Broekema M.Brouwer AJ.Still WC.Liskamp RMJ. Angew. Chem. Int. Ed. 1998, 37: 1846 -
4a
Brouwer AJ.Van der Linden HJ.Liskamp RMJ. J. Org. Chem. 2000, 65: 1750 -
4b
Gennari C.Ceccarelli S.Piariulli P.Montalbetti CAGN.Jackson RFW. J. Org. Chem. 1998, 63: 5312 - 5
Brouwer AJ.Liskamp RMJ. J. Org. Chem. 2004, 69: 3662 -
6a
Monnee MCF.Marijne MF.Brouwer AJ.Liskamp RMJ. Tetrahedron Lett. 2000, 41: 7991 -
6b
Monnee MCF.Marijne MF.Brouwer AJ.Liskamp RMJ. Tetrahedron Lett. 2001, 42: 965 -
6c
De Jong R.Rijkers DTS.Liskamp RMJ. Helv. Chim. Acta 2002, 85: 4230 - 7
Uddin MdJ.Rao PNP.Knaus RE. Bioorg. Med. Chem. 2003, 11: 5273 - For thermolysis reactions of sulfonyl azides, see :
-
8a
Breslow DS.Sloan MF.Newburg NR.Renfrow WB. J. Am. Chem. Soc. 1968, 91: 2273 -
8b
Abramovitch RA.Holcomb WD.Wake S. J. Am. Chem. Soc. 1981, 103: 1525 -
8c
McManus SP.Smith MR.Abramovitch RA.Offor MN. J. Org. Chem. 1984, 49: 683 -
8d
Abramovitch RA.Kress AO.McManus SP.Smith MR. J. Org. Chem. 1984, 49: 3114 -
8e
Abramovitch RA.Holcomb WD.Thompson WM.Wake S. J. Org. Chem. 1984, 49: 5124 -
8f
El-Sayed RA. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 237 -
9a
Panchaud P.Chabaud L.Landais Y.Ollivier C.Renauld P.Zigmantas S. Chem. Eur. J. 2004, 10: 3606 -
9b
Boteju LW.Wegner K.Hruby VJ. Tetrahedron Lett. 1992, 33: 7491 -
9c
Evans DA.Britton TC.Ellman JA.Dorow RL. J. Am. Chem. Soc. 1990, 112: 4011 - For the use of sulfonyl azides in diazo transfer reactions, see:
-
10a
Danheiser RL.Miller RF.Brisbois RG. Org. Synth., Coll. Vol. IX 1998, 134 ; and references cited therein -
10b
Anselme J.-P.Fischer W. Tetrahedron 1969, 25: 855 - 11 For addition of sulfonyl azides to double bonds, see:
Zalkow LH.Oehlschlager AC. J. Org. Chem. 1963, 28: 3303 -
12a
Leffler JE.Tsuno Y. J. Org. Chem. 1963, 28: 902 -
12b
Andersen NG.Ramsden PD.Che D.Parvez M.Keay BA. Org. Lett. 1999, 1: 2009 - 13
Shangguan N.Katukojvala S.Greenberg R.Williams LJ. J. Am. Chem. Soc. 2003, 125: 7754 - 14
Merkx R.Brouwer AJ.Rijkers DTS.Liskamp RMJ. Org. Lett. 2005, 7: 1125 - 15 For a review on the Staudinger reaction, see:
Gololobov YG.Kasukhin LF. Tetrahedron 1992, 48: 1353 - 16
von Arx E.Faupel M.Bruggen M. J. Chromatogr. 1976, 120: 224
References
In the NMR spectra, also broad, low-intensity signals were observed, presumably due to the presence of the minor Fmoc rotamer.