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

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Synthesis 2004(15): 2523-2526
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;

Further Information

Publication History

Received 26 April 2004
Publication Date:
19 August 2004 (online)

Abstract
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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

References

1a Lewis MD. Cha JK. Kishi Y. J. Am. Chem. Soc. 1982, 104: 4976

Article in Thieme Connect Google Scholar
1b Paterson L. Keown LE. Tetrahedron Lett. 1997, 38: 5727

Article in Thieme Connect Google Scholar
1c Horita K. Sakkurai Y. Nagasawa M. Hacliya S. Yonemistu O. Synlett 1994, 43

Article in Thieme Connect Google Scholar
2a Weatherman RV. Mortell KH. Chervenak M. Kiessling LL. Toone E. J. Biochem. 1996, 35: 3619

Crossref Google Scholar
2b Levy DE. Tan C. The Chemistry of C-Glycosides Pergamon Press; Oxford: 1995.

Crossref Google Scholar
3a Du Y. Linhardt RJ. Tetrahedron 1998, 54: 9913

Google Scholar
3b Nicolaou KC. Duggan ME. Hwang CK. Somers PK. J. Chem. Soc., Chem. Commun. 1985, 1359

Google Scholar
3c Wincott FE. Danishefsky SJ. Schutte G. Tetrahedron Lett. 1987, 28: 4951

Google Scholar
3d Andersen L. Mikkelsen LM. Beau JM. Skrydstrup T. Synlett 1998, 1393

Google Scholar
3e Mazeas D. Skrydstrup T. Beau JM. Angew. Chem., Int. Ed. Engl. 1995, 909

Google Scholar
4a Suhadolnik RJ. Nucleoside Antibiotics Wiley-Interscience; New York: 1970.

Google Scholar
4b Hanessian SC. Total Synthesis of Natural Products: The Chiron Approach Pergamon Press; Oxford: 1984.

Google Scholar
5a Danishefsky SJ. Keerwin JF. J. Org. Chem. 1982, 47: 3803

Crossref Google Scholar
5b De Raadt A. Griegl H. Klempic N. Stutz AE. J. Org. Chem. 1993, 58: 3179

Crossref Google Scholar
5c De LasHeras FG. Felix AS. Ferdanzandez-Risa P. Tetrahedron 1983, 39: 1617

Crossref Google Scholar
5d Kunz H. Weibmuller J. Muller B. Tetrahedron Lett. 1984, 25: 3571

Crossref Google Scholar
6a Dawe RD. Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1981, 1180

Crossref Google Scholar
6b Toshima K. Ishizuka T. Matsuo G. Nakata M. Chem. Lett. 1993, 2013

Crossref Google Scholar
6c Toshima K. Miyamito N. Matsuo G. Nakata M. Matsumura S. Chem. Commun. 1996, 1379

Crossref Google Scholar
7a Hayashi M. Kawabata H. Inoue K. Carbohydr. Res. 2000, 325: 68

Crossref Google Scholar
7b Takhi M. Adel A.-HAR. Schimdt RR. Tetrahedron Lett. 2001, 42: 4053

Crossref Google Scholar
7c Yadav JS. Reddy BVS. Chand PK. Tetrahedron Lett. 2001, 42: 4057

Crossref Google Scholar
8 Leonard MN. Wieland LC. Mohan RS. Tetrahedron 2002, 58: 8373

Crossref Google Scholar
9 Repichet S. Zwick A. Vendier L. Le Roux C. Dubac J. Tetrahedron Lett. 2002, 43: 993

Crossref Google Scholar
10a Macro-Conlelles JL. Farnandez C. Gomez A. Martin-Leon N. Tetrahedron Lett. 1990, 31: 1467

Crossref Google Scholar
10b Ichikawa Y. Isobe M. Konobe M. Goto T. Carbohydr. Res. 1987, 171: 193

Crossref Google Scholar
10c Hosokawa S. Krischbaum B. Isobe M. Tetrahedron Lett. 1998, 39: 1917

Crossref Google Scholar