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
References
<A NAME="RZ13805SS-1">1 </A>
Brouwer AJ.
Monnee MCF.
Liskamp RMJ.
Synthesis
2000,
1579
<A NAME="RZ13805SS-2A">2a </A>
De Bont DBA.
Dijkstra GDH.
den Hartog JAJ.
Liskamp RMJ.
Bioorg. Med. Chem. Lett.
1996,
6:
3035
<A NAME="RZ13805SS-2B">2b </A>
De Bont DBA.
Moree WJ.
Liskamp RMJ.
Bioorg. Med. Chem.
1996,
4:
667
<A NAME="RZ13805SS-2C">2c </A>
De Bont DBA.
Sliedregt-Bol KM.
Hofmeyer LJF.
Liskamp RMJ.
Bioorg. Med. Chem.
1999,
7:
1043
<A NAME="RZ13805SS-2D">2d </A>
Liskamp RMJ.
Kruijtzer JAW.
Mol. Diversity
2004,
8:
79
<A NAME="RZ13805SS-3A">3a </A>
Löwik DWPM.
Mulders SJE.
Cheng Y.
Shao Y.
Liskamp RMJ.
Tetrahedron Lett.
1996,
37:
8253
<A NAME="RZ13805SS-3B">3b </A>
Löwik DWPM.
Weingarten MD.
Broekema M.
Brouwer AJ.
Still WC.
Liskamp RMJ.
Angew. Chem. Int. Ed.
1998,
37:
1846
<A NAME="RZ13805SS-4A">4a </A>
Brouwer AJ.
Van der Linden HJ.
Liskamp RMJ.
J. Org. Chem.
2000,
65:
1750
<A NAME="RZ13805SS-4B">4b </A>
Gennari C.
Ceccarelli S.
Piariulli P.
Montalbetti CAGN.
Jackson RFW.
J. Org. Chem.
1998,
63:
5312
<A NAME="RZ13805SS-5">5 </A>
Brouwer AJ.
Liskamp RMJ.
J. Org. Chem.
2004,
69:
3662
<A NAME="RZ13805SS-6A">6a </A>
Monnee MCF.
Marijne MF.
Brouwer AJ.
Liskamp RMJ.
Tetrahedron Lett.
2000,
41:
7991
<A NAME="RZ13805SS-6B">6b </A>
Monnee MCF.
Marijne MF.
Brouwer AJ.
Liskamp RMJ.
Tetrahedron Lett.
2001,
42:
965
<A NAME="RZ13805SS-6C">6c </A>
De Jong R.
Rijkers DTS.
Liskamp RMJ.
Helv. Chim. Acta
2002,
85:
4230
<A NAME="RZ13805SS-7">7 </A>
Uddin MdJ.
Rao PNP.
Knaus RE.
Bioorg. Med. Chem.
2003,
11:
5273
For thermolysis reactions of sulfonyl azides, see :
<A NAME="RZ13805SS-8A">8a </A>
Breslow DS.
Sloan MF.
Newburg NR.
Renfrow WB.
J. Am. Chem. Soc.
1968,
91:
2273
<A NAME="RZ13805SS-8B">8b </A>
Abramovitch RA.
Holcomb WD.
Wake S.
J. Am. Chem. Soc.
1981,
103:
1525
<A NAME="RZ13805SS-8C">8c </A>
McManus SP.
Smith MR.
Abramovitch RA.
Offor MN.
J. Org. Chem.
1984,
49:
683
<A NAME="RZ13805SS-8D">8d </A>
Abramovitch RA.
Kress AO.
McManus SP.
Smith MR.
J. Org. Chem.
1984,
49:
3114
<A NAME="RZ13805SS-8E">8e </A>
Abramovitch RA.
Holcomb WD.
Thompson WM.
Wake S.
J. Org. Chem.
1984,
49:
5124
<A NAME="RZ13805SS-8F">8f </A>
El-Sayed RA.
Phosphorus, Sulfur Silicon Relat. Elem.
2004,
179:
237
<A NAME="RZ13805SS-9A">9a </A>
Panchaud P.
Chabaud L.
Landais Y.
Ollivier C.
Renauld P.
Zigmantas S.
Chem. Eur. J.
2004,
10:
3606
<A NAME="RZ13805SS-9B">9b </A>
Boteju LW.
Wegner K.
Hruby VJ.
Tetrahedron Lett.
1992,
33:
7491
<A NAME="RZ13805SS-9C">9c </A>
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:
<A NAME="RZ13805SS-10A">10a </A>
Danheiser RL.
Miller RF.
Brisbois RG.
Org. Synth., Coll. Vol. IX
1998,
134 ; and references cited therein
<A NAME="RZ13805SS-10B">10b </A>
Anselme J.-P.
Fischer W.
Tetrahedron
1969,
25:
855
<A NAME="RZ13805SS-11">11 </A> For addition of sulfonyl azides to double bonds, see:
Zalkow LH.
Oehlschlager AC.
J. Org. Chem.
1963,
28:
3303
<A NAME="RZ13805SS-12A">12a </A>
Leffler JE.
Tsuno Y.
J. Org. Chem.
1963,
28:
902
<A NAME="RZ13805SS-12B">12b </A>
Andersen NG.
Ramsden PD.
Che D.
Parvez M.
Keay BA.
Org. Lett.
1999,
1:
2009
<A NAME="RZ13805SS-13">13 </A>
Shangguan N.
Katukojvala S.
Greenberg R.
Williams LJ.
J. Am. Chem. Soc.
2003,
125:
7754
<A NAME="RZ13805SS-14">14 </A>
Merkx R.
Brouwer AJ.
Rijkers DTS.
Liskamp RMJ.
Org. Lett.
2005,
7:
1125
<A NAME="RZ13805SS-15">15 </A> For a review on the Staudinger reaction, see:
Gololobov YG.
Kasukhin LF.
Tetrahedron
1992,
48:
1353
<A NAME="RZ13805SS-16">16 </A>
von Arx E.
Faupel M.
Bruggen M.
J. Chromatogr.
1976,
120:
224
<A NAME="RZ13805SS-17">17 </A>
In the NMR spectra, also broad, low-intensity signals were observed, presumably due
to the presence of the minor Fmoc rotamer.