RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(7): 1058-1060
DOI: 10.1055/s-2005-861843
DOI: 10.1055/s-2005-861843
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Highly Symmetrical Amino Acid-Derived N,N′-Diacylated Sulfodiimines
Weitere Informationen
Received
13 December 2004
Publikationsdatum:
10. März 2005 (online)
Publikationsverlauf
Publikationsdatum:
10. März 2005 (online)
Abstract
A mild and efficient method for the coupling of sulfodiimines with N-protected amino acids has been developed, yielding the corresponding N,N′-diacylated sulfodiimines with up to 94% yield.
Key words
coupling - amino acids - acylations - peptides - sulfodiimines - asymmetric synthesis
- Reviews:
-
1a
Reggelin M.Zur C. Synthesis 2000, 1 -
1b
Mikolajczk M.Drabowicz J.Kielbasinski P. Chiral Sulfur Reagents CRC Press; Boca Raton: 1997. -
1c
Pyne S. Sulfur Reports 1992, 12: 57 -
1d
Haake M. In Houben-Weyl, Methoden der organischen Chemie Vol. E11:Klamann D. Thieme; Stuttgart: 1985. p.1299 -
1e
Johnson CR. Acc. Chem. Res. 1973, 6: 341 -
1f
Johnson CR. Aldrichimica Acta 1985, 18: 3 - For some recent examples stemming from this group, see:
-
2a
Bolm C.Müller D.Dalhoff C.Hackenberger CPR.Weinhold E. Bioorg. Med. Chem. Lett. 2003, 13: 3207 -
2b
Bolm C.Müller D.Hackenberger CPR. Org. Lett. 2002, 4: 893 -
2c
Bolm C.Moll G.Kahmann JD. Chem.-Eur. J. 2001, 7: 1118 - 3
Okamura H.Bolm C. Chem. Lett. 2004, 33: 482 - For recent examples, see:
-
4a
Langner M.Bolm C. Angew. Chem. Int. Ed. 2004, 43: 5984 -
4b
Bolm C.Martin M.Simic O.Verrucci M. Org. Lett. 2003, 5: 427 -
4c
Bolm C.Verrucci M.Simic O.Cozzi PG.Raabe G.Okamura H. Chem. Commun. 2003, 2816 -
4d
Bolm C.Simic O. J. Am. Chem. Soc. 2001, 123: 3830 -
4e
Bolm C.Simic O.Martin M. Synlett 2001, 1878 -
4f
Harmata M.Ghosh SK. Org. Lett. 2001, 3: 3321 -
4g See also:
Bolm C.Martin M.Gescheidt G.Palivan C.Neshchadin D.Bertagnolli H.Feth M.Schweiger A.Mitrikas G.Harmer J. J. Am. Chem. Soc. 2003, 125: 6222 - 5
Harmata M. Chemtracts: Org. Chem. 2003, 16: 660 - 6 Review:
Haake M. In Topics in Sulfur ChemistrySenning A. Thieme; Stuttgart: 1976. Vol. 1. p.185 - 7
Diederich WE.Haake M. J. Org. Chem. 2003, 68: 3817 ; and references therein - 8 To the best of our knowledge, there is only one single report on the synthesis of a non-racemic sulfodiimine, and in this case, the enantiomer ratio has not been determined:
Christensen BW.Kjær A. J. Chem. Soc., Chem. Commun. 1975, 784 - 9
Haake M.Fode H.Eichenauer B. Liebigs Ann. Chem. 1972, 759: 107 - 10
Hackenberger CPR.Raabe G.Bolm C. Chem.-Eur. J. 2004, 10: 2942 ; and references therein - For reviews on coupling reagents, see:
-
11a
Han S.-Y.Kim Y.-A. Tetrahedron 2004, 60: 2447 -
11b
Klausner YS.Bodansky M. Synthesis 1972, 453
References
In this case, the meso-product resulting from an epimerization would possess two diastereotopic methyl groups. Those would be in rather different chemical and electronic environments and, therefore, two different chemical shifts would be likely to occur in the 1H NMR spectrum.