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Synlett 2012(4): 541-544
DOI: 10.1055/s-0031-1290327
DOI: 10.1055/s-0031-1290327
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Organocatalytic Conversion of Ribose and Other Protected Carbohydrate Derivatives into 2-Deoxy-lactones
Further Information
Received
31 October 2011
Publication Date:
27 January 2012 (online)
Publication History
Publication Date:
27 January 2012 (online)
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Abstract
We report the simultaneous reduction of the 2-position and oxidation of the anomeric position in several protected furanosyl and pyranosyl sugar derivatives, mediated through NHC catalysis. This reaction allows the one-step access to highly valuable 2-deoxy-sugars from abundant 2-oxygenated sugar derivatives.
Key words
carbenes - deoxygenation - green chemistry - isomerization - umpolung
- 1
De Mesmaeker A.Lebreton J.Jouanno C.Fritsch V.Wolf RM.Wendeborn S. Synlett 1997, 1287 - 2
Wendeborn S.Jouanno C.Wolf RM.De Mesmaeker A. Tetrahedron Lett. 1996, 37: 5511 - 3
Wendeborn S.Wolf RM.De Mesmaeker A. Tetrahedron Lett. 1995, 36: 6879 - 4
Enders D.Niemeier O.Henseler A. Chem. Rev. 2007, 107: 5606 - 5
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 - 6
Vora HU.Rovis T. Aldrichimica Acta 2011, 44: 3 - 7
Nair V.Menon RS.Biju AT.Sinu CR.Paul RR.Jose A.Sreekumarc V. Chem. Soc. Rev. 2011, 40: 5336 - 8
Biju AT.Kuhl N.Glorius F. Acc. Chem. Res. 2011, 44: 1182 - 9
Breslow R. J. Am. Chem. Soc. 1958, 80: 3719 -
10a
Barton DHR.Motherwell WB. Pure Appl. Chem. 1981, 53: 15 -
10b
Barton DHR.Jaszberenyi JC. Tetrahedron Lett. 1989, 30: 2619 - 11
Chow KY.-K.Bode JW. J. Am. Chem. Soc. 2004, 126: 8126 - 12
Reynolds NT.Read de Alaniz J.Rovis T. J. Am. Chem. Soc. 2004, 126: 9518 - 13
Thai K.Li W.Dudding T.Bilodeau F.Gravel M. Org. Lett. 2010, 12: 5708 - 14
Kim Y.-J.Streitwieser A. J. Am. Chem. Soc. 2002, 124: 5757 - 15 For calculated pK
a of
NHC, see:
Magill AM.Cavell KJ.Yates BF. J. Am. Chem. Soc. 2004, 126: 8717 - 16 For a review on characteristics
of NHC, see:
Dröge T.Glorius F. Angew. Chem. Int. Ed. 2010, 49: 6940 -
17a
Spectroscopic Data for Compound 17
¹H NMR (400 MHz, DMSO-d 6): δ = 2.22 (dd, J = 17.61, 2.20 Hz, 1 H), 2.81 (dd, J = 17.79, 6.42 Hz, 1 H), 3.47-3.62 (m, 2 H), 4.21-4.32 (m, 2 H), 5.06 (t, J = 5.50 Hz, 1 H), 5.49 (d, J = 4.03 Hz, 1 H). -
17b Compound 17 isolated
from the NHC-catalyzed rearrangement was identical to
that of an authentic sample purchased from Carbosynth (www.carbosynth.com;
catalog number MD00127) and to spectral data reported in:
Miranda PO.Estévez F.Quintana J.García CI.Brouard I.Padrón JI.Pivel JP.Bermejo J. J. Med. Chem. 2004, 47: 292 - 18
Grasa GA.Güveli T.Singh R.Nolan SP. J. Org. Chem. 2003, 68: 2812