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Synthesis 2015; 47(15): 2249-2255
DOI: 10.1055/s-0034-1380416
DOI: 10.1055/s-0034-1380416
special topic
Amine-Catalyzed Cascade Reactions of Unprotected and Unactivated Carbohydrates: Direct Access to C-Glycosides
Authors
Further Information
Publication History
Received: 12 March 2015
Accepted after revision: 16 April 2015
Publication Date:
19 May 2015 (online)
Abstract
Unprotected carbohydrates were reacted in amine-catalyzed cascade reactions with various methyl ketones to give a direct access to C-glycosides by an operationally simple protocol. As the reaction mechanism, an aldol condensation followed by an intramolecular conjugate addition is assumed.
Key words
C-glycosides - unprotected carbohydrates - amine catalysis - cascade reaction - intramolecular conjugate additionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380416.
- Supporting Information (PDF)
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References
- 1 Soengas RG, Otero JM, Estévez AM, Rauter AP, Cachatra V, Estévez JC, Estévez RJ. Carbohydr. Chem. 2012; 38: 263
- 3a Hanessian S, Pernet AG. Can. J. Chem. 1974; 52: 1280
- 3b Hanessian S, Pernet AG. Can. J. Chem. 1974; 52: 1266
- 3c Ogawa T, Pernet AG, Hanessian S. Tetrahedron Lett. 1973; 3543
- 3d Pernet AG, Ogawa T, Hanessian S. Tetrahedron Lett. 1973; 3547
- 4a Gao J, Martichonok V, Whitesides GM. J. Org. Chem. 1996; 61: 9538
- 4b Spevak W, Dasgupta F, Hobbs CJ, Nagy JO. J. Org. Chem. 1996; 61: 3417
- 4c Kim E, Gordon DM, Schmid W, Whitesides GM. J. Org. Chem. 1993; 58: 5500
Reference Ris Wihthout Link
- 4d Gordon DM, Whitesides GM. J. Org. Chem. 1993; 58: 7937
- 5 Haines AH, Lamb AJ. Carbohydr. Res. 2000; 325: 323
- 6a van Kalkeren HA, van Rootselaar S, Haasjes FS, Rutjes FP. J. T, van Delft FL. Carbohydr. Res. 2012; 362: 30
- 6b Lievre C, Humez S, Frechou C, Demailly G. Tetrahedron Lett. 1997; 38: 6003
- 6c Railton CJ, Clive DL. J. Carbohydr. Res. 1996; 281: 69
- 6d Horton D, Koh D. Carbohydr. Res. 1993; 250: 231
- 6e Lee HW, Lee IY. C, Park IH. Bull. Korean Chem. Soc. 1992; 13: 222 ; Chem. Abstr. 1992, 117, 151217
- 6f Henk T, Giannis A, Sandhoff K. Liebigs Ann. Chem. 1992; 167
- 6g Sun KM, Dawe RD, Fraser-Reid B. Carbohydr. Res. 1987; 171: 35
- 6h Schoenenberger B, Summermatter W, Ganter C. Helv. Chim. Acta 1982; 65: 2333
- 6i Cachatra V, Rauter AP. Curr. Org. Chem. 2014; 18: 1731
- 6j Zhdanov YA, Alekseev YE, Alekseeva VG. Adv. Carbohydr. Chem. 1972; 27: 227
- 6k Kotchekow NK, Dimitriev BA. Tetrahedron 1965; 21: 803
- 7a Ranoux A, Lemiegre L, Benoit M, Guegan JP, Benvegnu T. Eur. J. Org. Chem. 2010; 1314
- 7b Ranoux A, Lemiegre L, Benvegnu T. Sci. China Chem. 2010; 53: 1957 ; Chem. Abstr. 2011, 154, 46218
- 8a Schmid W, Whitesides GM. J. Am. Chem. Soc. 1991; 113: 6674
- 8b Kim E, Gordon DM, Schmid W, Whitesides GM. J. Org. Chem. 1993; 58: 5500
Reference Ris Wihthout Link
- 8c Gordon DM, Whitesides GM. J. Org. Chem. 1993; 58: 7937
- 8d Gao J, Martichonok V, Whitesides GM. J. Org. Chem. 1996; 61: 9538
- 8e Spevak W, Dasgupta F, Hobbs CJ, Nagy JO. J. Org. Chem. 1996; 61: 3417
- 8f Palmelund A, Madsen R. J. Org. Chem. 2005; 70: 8248
- 8g Saloranta T, Müller C, Vogt D, Leino R. Chem. Eur. J. 2008; 14: 10539
- 8h Toshima K, Ishizuka T, Matsuo G, Nakata M. Tetrahedron Lett. 1994; 35: 5673
- 9a Rodridues F, Canac Y, Lubineau A. Chem. Commun. 2000; 2049
- 9b Gonzalez MA, Requejo JL. J, Albarran JC. P, Perez JA G. Carbohydr. Res. 1986; 158: 53
- 9c Wulff G, Clarkson G. Carbohydr. Res. 1994; 257: 81
- 10a Feng W, Fang Z, Yang J, Zheng B, Jiang Y. Carbohydr. Res. 2011; 346: 352
- 10b Wang J, Li Q, Ge Z, Li R. Tetrahedron 2012; 68: 1315
- 11a Riafrecha LE, Rodriguez OM, Vullo D, Supuran CT, Colinas PA. Bioorg. Med. Chem. 2014; 22: 5308
- 11b Hemamalini A, Das TM. New J. Chem. 2014; 38: 3015
- 11c Xia T.-Y, Li Y.-B, Yin Z.-J, Meng X.-B, Li S.-C, Li Z.-J. Chin. Chem. Lett. 2014; 25: 1220 ; Chem. Abstr. 2014, 161, 474400
- 11d Palasz A, Kalinowska-Tluscik J, Jablonski M. Tetrahedron 2013; 69: 8216
- 11e Ajay A, Sharma S, Gupt MP, Bajpai V, Hamidullah KB, Kaushik MP, Konwar R, Ampapathi RS, Tripathi RP. Org. Lett. 2012; 14: 4306
- 11f Yan L, Xu H, Liu F, Zhao J, Liu H. Chin. J. Chem. 2012; 30: 914 ; Chem. Abstr. 2012, 157, 165731
- 11g Liu L, Abdel MB, Schmidt-Supprian M, Pohl NL. B. J. Org. Chem. 2012; 77: 1539
- 11h Mugunathan B, Ramakrishna K, Sriram D, Yogeeswari PI, Ravindranathan KK. P. Bioorg. Med. Chem. Lett. 2011; 21: 3947
- 11i Giguere D, Andre S, Bonin M.-A, Bellefleur M.-A, Provencal A, Cloutier P, Pucci B, Roy R, Gabius H.-J. Bioorg. Med. Chem. 2011; 19: 3280
- 11j Hemamalini A. Carbohydr. Res. 2011; 346: 1914
- 11k Foley PM, Phimphachanh A, Beach ES, Zimmerman JB, Anastas PT. Green Chem. 2011; 13: 321
- 11l Carpenter CA, Kenar JA, Price NP. J. Green Chem. 2010; 12: 2012
- 11m Price NP. J. Anal. Chem. 2010; 82: 2863
- 11n Cavezza A, Boulle C, Gueguiniat A, Pichaud P, Trouille S, Ricard L, Dalko-Csiba M. Bioorg. Med. Chem. Lett. 2009; 19: 845
- 11o Bragnier N, Guillot R, Scherrmann M.-C. Org. Biomol. Chem. 2009; 7: 3918
- 11p Wang J.-f, Lei M, Li Q, Ge Z.-m, Wang X, Li R.-t. Tetrahedron 2009; 65: 4826
- 11q Nagarajan S, Das TM. Carbohydr. Res. 2009; 344: 1028
- 11r Giguere D, Bonin M.-A, Cloutier P, Patnam R, St-Pierre C, Sato S, Roy R. Bioorg. Med. Chem. 2008; 16: 7811
- 11s Norsikian S, Zeitouni J, Rat S, Gerard S, Lubineau A. Carbohydr. Res. 2007; 342: 2716
- 11t Bragnier N, Scherrmann M.-C. Synthesis 2005; 814
- 11u Hersant Y, Abou-Jneid R, Canac Y, Lubineau A, Philippe M, Semeria D, Radisson X, Scherrmann M.-C. Carbohydr. Res. 2004; 339: 741
- 11v Zeitouni J, Norsikian S, Lubineau A. Tetrahedron Lett. 2004; 45: 7761
- 11w Riemann I, Papadopoulos MA, Knorst M, Fessner W.-D. Aust. J. Chem. 2002; 55: 147
- 12a Bartoli G, Fernandez-Bolanos JG, Di Antonio G, Foglia G, Giuli S, Gunnella R, Mancinelli M, Marcantoni E, Paoletti M. J. Org. Chem. 2007; 72: 6029; and references cited therein
- 12b Garcia Gonzalez F, Gomez Sanchez A. Adv. Carbohydr. Chem. 1965; 20: 303
- 12c Garcia Gonzalez F. Adv. Carbohydr. Chem. 1956; 11: 97
- 13 Scherrmann MC. Top. Curr. Chem. 2010; 295: 1
- 14 See Supporting Information
- 15a Voigt B, Mahrwald R. Chem. Commun. 2014; 50: 817
- 15b Vasiloiu M, Rainer D, Gaertner P, Reichel C, Schroeder C, Bica K. Catal. Today 2013; 200: 80
- 15c Hu Z.-p, Zhang J.-m, Lou C.-l, Wang J.-j, Nie S.-z, Yan M. ARKIVOC 2010; (x): 17
- 15d Vesely J, Rios R, Cordova A. Tetrahedron Lett. 2008; 49: 1137
- 15e Amedjkouh M. Tetrahedron: Asymmetry 2007; 18: 390
- 15f Pihko PM, Laurikainen KM, Usano A, Nyberg AI, Kaavi JA. Tetrahedron 2006; 62: 317
- 16a Lambert JB, Lu G, Singer SR, Kolb VM. J. Am. Chem. Soc. 2004; 126: 9611
- 16b Qrtiz P, Reguera E, Fernandez-Bertran J. J. Fluorine Chem. 2002; 113: 7
- 16c Angyal SJ. Carbohydr. Res. 1994; 263: 1
- 16d Lemieux RU, Anderson L, Conner AH. Carbohydr. Res. 1971; 20: 59
- 16e Lemieux RU, Stevens JD. Can. J. Chem. 1966; 44: 249
- 16f Bauer H, Brinkmeier A, Buddrus J, Jablonowski M. Liebigs Ann. Chem. 1986; 1804
- 16g Breitmaier E, Hollstein U. Org. Magn. Res. 1976; 8: 573
For reviews in this field, see:
For early cascade reactions (Knoevenagel/intramolecular oxa-Michael addition) of unprotected and unactivated carbohydrates with barbituric acid derivatives, see: