Bi(OTf)3 as Novel and Efficient Catalyst for the Stereoselective Synthesis of C-Pseudoglycals

J. S. Yadav; B. V. S. Reddy; K. Srinivasa Reddy; L. Chandraiah; V. Sunitha

doi:10.1055/s-2004-831187

PAPER

Bi(OTf)₃ as Novel and Efficient Catalyst for the Stereoselective Synthesis of C-Pseudoglycals

J. S. Yadav*, B. V. S. Reddy, K. Srinivasa Reddy, L. Chandraiah, V. Sunitha
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;

Abstract

All articles of this category

Abstract

d-Glycals undergo smoothly allylic rearrangement with allyltrimethylsilane and trimethylsilyl cyanide in the presence of catalytic amount of bismuth triflateto 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

Full Text

References

<A NAME="RZ08204SS-1A">1a</A> Lewis MD. Cha JK. Kishi Y. J. Am. Chem. Soc. 1982, 104: 4976

<A NAME="RZ08204SS-1B">1b</A> Paterson L. Keown LE. Tetrahedron Lett. 1997, 38: 5727

<A NAME="RZ08204SS-1C">1c</A> Horita K. Sakkurai Y. Nagasawa M. Hacliya S. Yonemistu O. Synlett 1994, 43

<A NAME="RZ08204SS-2A">2a</A> Weatherman RV. Mortell KH. Chervenak M. Kiessling LL. Toone E. J. Biochem. 1996, 35: 3619

<A NAME="RZ08204SS-2B">2b</A> Levy DE. Tan C. The Chemistry of C-Glycosides Pergamon Press; Oxford: 1995.

<A NAME="RZ08204SS-3A">3a</A> Du Y. Linhardt RJ. Tetrahedron 1998, 54: 9913

<A NAME="RZ08204SS-3B">3b</A> Nicolaou KC. Duggan ME. Hwang CK. Somers PK. J. Chem. Soc., Chem. Commun. 1985, 1359

<A NAME="RZ08204SS-3C">3c</A> Wincott FE. Danishefsky SJ. Schutte G. Tetrahedron Lett. 1987, 28: 4951

<A NAME="RZ08204SS-3D">3d</A> Andersen L. Mikkelsen LM. Beau JM. Skrydstrup T. Synlett 1998, 1393

<A NAME="RZ08204SS-3E">3e</A> Mazeas D. Skrydstrup T. Beau JM. Angew. Chem., Int. Ed. Engl. 1995, 909

<A NAME="RZ08204SS-4A">4a</A> Suhadolnik RJ. Nucleoside Antibiotics Wiley-Interscience; New York: 1970.

<A NAME="RZ08204SS-4B">4b</A> Hanessian SC. Total Synthesis of Natural Products: The Chiron Approach Pergamon Press; Oxford: 1984.

<A NAME="RZ08204SS-5A">5a</A> Danishefsky SJ. Keerwin JF. J. Org. Chem. 1982, 47: 3803

<A NAME="RZ08204SS-5B">5b</A> De Raadt A. Griegl H. Klempic N. Stutz AE. J. Org. Chem. 1993, 58: 3179

<A NAME="RZ08204SS-5C">5c</A> De LasHeras FG. Felix AS. Ferdanzandez-Risa P. Tetrahedron 1983, 39: 1617

<A NAME="RZ08204SS-5D">5d</A> Kunz H. Weibmuller J. Muller B. Tetrahedron Lett. 1984, 25: 3571

<A NAME="RZ08204SS-6A">6a</A> Dawe RD. Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1981, 1180

<A NAME="RZ08204SS-6B">6b</A> Toshima K. Ishizuka T. Matsuo G. Nakata M. Chem. Lett. 1993, 2013

<A NAME="RZ08204SS-6C">6c</A> Toshima K. Miyamito N. Matsuo G. Nakata M. Matsumura S. Chem. Commun. 1996, 1379

<A NAME="RZ08204SS-7A">7a</A> Hayashi M. Kawabata H. Inoue K. Carbohydr. Res. 2000, 325: 68

<A NAME="RZ08204SS-7B">7b</A> Takhi M. Adel A.-HAR. Schimdt RR. Tetrahedron Lett. 2001, 42: 4053

<A NAME="RZ08204SS-7C">7c</A> Yadav JS. Reddy BVS. Chand PK. Tetrahedron Lett. 2001, 42: 4057

<A NAME="RZ08204SS-8">8</A> Leonard MN. Wieland LC. Mohan RS. Tetrahedron 2002, 58: 8373

<A NAME="RZ08204SS-9">9</A> Repichet S. Zwick A. Vendier L. Le Roux C. Dubac J. Tetrahedron Lett. 2002, 43: 993

<A NAME="RZ08204SS-10A">10a</A> Macro-Conlelles JL. Farnandez C. Gomez A. Martin-Leon N. Tetrahedron Lett. 1990, 31: 1467

<A NAME="RZ08204SS-10B">10b</A> Ichikawa Y. Isobe M. Konobe M. Goto T. Carbohydr. Res. 1987, 171: 193

<A NAME="RZ08204SS-10C">10c</A> Hosokawa S. Krischbaum B. Isobe M. Tetrahedron Lett. 1998, 39: 1917