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Synthesis 2004(15): 2523-2526
DOI: 10.1055/s-2004-831187
DOI: 10.1055/s-2004-831187
PAPER
© Georg Thieme Verlag Stuttgart · New YorkBi(OTf)3 as Novel and Efficient Catalyst for the Stereoselective Synthesis of C-Pseudoglycals
Further Information
Received
26 April 2004
Publication Date:
19 August 2004 (online)
Publication History
Publication Date:
19 August 2004 (online)

Abstract
d-Glycals undergo smoothly allylic rearrangement with allyltrimethylsilane and trimethylsilyl cyanide in the presence of catalytic amount of bismuth triflate to afford the corresponding 2,3-unsaturated allyl glycosides and glycosyl cyanides in excellent yields with high α-selectivity.
Key words
bismuth reagents - glycals - pseudoglycals - C-glycosides
- 1a
Lewis MD.Cha JK.Kishi Y. J. Am. Chem. Soc. 1982, 104: 4976 - 1b
Paterson L.Keown LE. Tetrahedron Lett. 1997, 38: 5727 - 1c
Horita K.Sakkurai Y.Nagasawa M.Hacliya S.Yonemistu O. Synlett 1994, 43 - 2a
Weatherman RV.Mortell KH.Chervenak M.Kiessling LL.Toone E. J. Biochem. 1996, 35: 3619 - 2b
Levy DE.Tan C. The Chemistry of C-Glycosides Pergamon Press; Oxford: 1995. - 3a
Du Y.Linhardt RJ. Tetrahedron 1998, 54: 9913 - 3b
Nicolaou KC.Duggan ME.Hwang CK.Somers PK. J. Chem. Soc., Chem. Commun. 1985, 1359 - 3c
Wincott FE.Danishefsky SJ.Schutte G. Tetrahedron Lett. 1987, 28: 4951 - 3d
Andersen L.Mikkelsen LM.Beau JM.Skrydstrup T. Synlett 1998, 1393 - 3e
Mazeas D.Skrydstrup T.Beau JM. Angew. Chem., Int. Ed. Engl. 1995, 909 - 4a
Suhadolnik RJ. Nucleoside Antibiotics Wiley-Interscience; New York: 1970. - 4b
Hanessian SC. Total Synthesis of Natural Products: The Chiron Approach Pergamon Press; Oxford: 1984. - 5a
Danishefsky SJ.Keerwin JF. J. Org. Chem. 1982, 47: 3803 - 5b
De Raadt A.Griegl H.Klempic N.Stutz AE. J. Org. Chem. 1993, 58: 3179 - 5c
De LasHeras FG.Felix AS.Ferdanzandez-Risa P. Tetrahedron 1983, 39: 1617 - 5d
Kunz H.Weibmuller J.Muller B. Tetrahedron Lett. 1984, 25: 3571 - 6a
Dawe RD.Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1981, 1180 - 6b
Toshima K.Ishizuka T.Matsuo G.Nakata M. Chem. Lett. 1993, 2013 - 6c
Toshima K.Miyamito N.Matsuo G.Nakata M.Matsumura S. Chem. Commun. 1996, 1379 - 7a
Hayashi M.Kawabata H.Inoue K. Carbohydr. Res. 2000, 325: 68 - 7b
Takhi M.Adel A.-HAR.Schimdt RR. Tetrahedron Lett. 2001, 42: 4053 - 7c
Yadav JS.Reddy BVS.Chand PK. Tetrahedron Lett. 2001, 42: 4057 - 8
Leonard MN.Wieland LC.Mohan RS. Tetrahedron 2002, 58: 8373 - 9
Repichet S.Zwick A.Vendier L.Le Roux C.Dubac J. Tetrahedron Lett. 2002, 43: 993 - 10a
Macro-Conlelles JL.Farnandez C.Gomez A.Martin-Leon N. Tetrahedron Lett. 1990, 31: 1467 - 10b
Ichikawa Y.Isobe M.Konobe M.Goto T. Carbohydr. Res. 1987, 171: 193 - 10c
Hosokawa S.Krischbaum B.Isobe M. Tetrahedron Lett. 1998, 39: 1917