Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York ZrCl4-Catalyzed Efficient Ferrier Glycosylation: A Facile Synthesis of Pseudoglycals G. Smitha, Ch. Sanjeeva Reddy*Department of Chemistry, Kakatiya University, Warangal-506 009, Indiae-Mail: chsrkuc@yahoo.co.in; Recommend Article Abstract Buy Article All articles of this category Abstract The reaction of tri-O-acetyl-d-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(IV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement. Key words zirconium(IV) chloride - Ferrier glycosylation - pseudoglycals Full Text References References 1a Ferrier RJ. Prasad N. J. Chem. Soc. C 1969, 570 1b For a recent review on the Ferrier rearrangement, see: Ferrier RJ. Topics Curr. Chem. 2001, 215: 153 1c For review on glycosidation, see: Toshima K. Tatsuta K. Chem. Rev. 1993, 93: 1503 2a Dorgan BJ. Jackson RFW. Synlett 1996, 859 2b Schmidt RR. Angerbauer R. Carbohydr. Res. 1981, 89: 159 2c Schmidt RR. Angerbauer R. Carbohydr. Res. 1981, 89: 193 2d Schmidt RR. Angerbauer R. Carbohydr. Res. 1979, 72: 272 2e Bracherro MP. Cabrera EF. Gomez GM. Peredes LMR. Carbohydr. Res. 1998, 181: 308 2f Danishefsky SJ. Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996, 120: 13515 2g Liu ZJ. Tetrahedron: Asymmetry 1999, 10: 2119 3 Williams NR. Wander JD. The Carbohydrates. Chemistry and Biochemistry Academic Press; New York: 1980. p.761 4a Descotes G. Martin J.-C. Carbohydr. Res. 1977, 56: 168 4b Klaffke W. Pudlo P. Springer D. Thiem J. Liebigs Ann. Chem. 1991, 6: 509 5a Grynkiewiez G. Priebe W. Zamojski A. Carbohydr. Res. 1979, 68: 33 5b Bhate P. Horton D. Priebe W. Carbohydr. Res. 1985, 144: 331 6 Toshima K. Ishizuka T. Matsuo G. Nakata M. Konoshita M. J. Chem. Soc., Chem. Commun. 1993, 704 7a Dawe RD. Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1981, 1180 7b Toshima K. Ishizuka T. Matsuo G. Nakata M. Tetrahedron Lett. 1994, 35: 5673 8 Fraser-Reid B. Madsen R. J. Org. Chem. 1995, 60: 3851 9a Babu BS. Balasubramanian KK. Tetrahedron Lett. 1999, 40: 5777 9b Yadav JS. Reddy BVS. Chandraiah L. Reddy KS. Carbohydr. Res. 2001, 332: 221 10 Schmidt RR. Hoffman M. Tetrahedron Lett. 1982, 23: 409 11a Toshima K. Miyamoto N. Matsuo G. Nakata M. Matsumura S. Chem. Commun. 1996, 1379 11b Shanmugasundaram B. Bose AK. Balasubramanian KK. Tetrahedron Lett. 2002, 43: 6795 12 Masson C. Soto J. Bessodes M. Synlett 2000, 1281 13a Babu BS. Balasubramanian KK. Tetrahedron Lett. 2000, 41: 1271 13b Yadav JS. Reddy BVS. Raman JV. Niranjan N. Kumar SK. Kunwar AC. Tetrahedron Lett. 2002, 43: 2095 13c Das SK. Reddy KA. Abbineni C. Roy J. Rao KVLN. Sachwani RH. Iqbal J. Tetrahedron Lett. 2003, 44: 4057 13d Das SK. Reddy KA. Roy J. Synlett 2003, 1607 14a Yadav JS. Reddy BVS. Synthesis 2002, 511 14b Yadav JS. Reddy BVS. Raju AK. Rao CV. Tetrahedron Lett. 2002, 43: 5437 15a Yadav JS. Reddy BVS. Murthy CVSR. Kumar GM. Synlett 2000, 1450 15b Yadav JS. Reddy BVS. Chand PK. Tetrahedron Lett. 2001, 42: 4057 15c Yadav JS. Reddy BVS. Geetha V. Synth. Commun. 2003, 33: 717 16a Takhi M. Abdel-Rahman AA.-H. Schmidt RR. Tetrahedron Lett. 2001, 42: 4053 16b Takhi M. Abdel-Rahman AA.-H. Schmidt RR. Synlett 2001, 427 17 Yadav JS. Reddy BVS. Reddy JSS. J. Chem. Soc., Perkin Trans. 1 2002, 2390 18 Yadav JS. Reddy BVS. Rao CV. Chand PK. Prasad AR. Synlett 2001, 1638 19 Pachamuthu K. Vankar YD. J. Org. Chem. 2001, 66: 7511 20 Swamy RN. Venkateshwarlu A. Synthesis 2002, 598 21 Bettadaiah BK. Srinivas P. Tetrahedron Lett. 2003, 44: 7257 22a Yadav JS. Reddy BVS. Reddy KB. Satyanarayana M. Tetrahedron Lett. 2002, 43: 7009 22b Danishefsky S. Kerwin JF. J. Org. Chem. 1982, 47: 3803 22c Babu BS. Balasubramanian KK. Carbohydr. Lett. 1999, 3: 339 23a Reddy ChS. Smitha G. Chandrasekhar S. Tetrahedron Lett. 2003, 44: 4693 23b Smitha G. Reddy ChS. Tetrahedron 2003, 59: 9571
