Abstract
Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position. These products have been found to be useful for a range of synthetic purposes. In particular, the C-glycosidic compounds have served as readily available starting materials for the preparation of useful non-carbohydrate compounds. While these allylic rearrangement processes are usually conducted under the influence of Lewis acid catalysts, adaptations that involve activation of the allylic substituents of the starting glycals as leaving groups under neutral conditions have been developed. General features of the reactions are described as well as applications in synthesis and extensions of the basic processes.
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8 References
(a) Danishefsky SJ, Bilodeau MK (1996) Angew Chem Int Ed Engl 35:289; (b) Bhattacharya SK, Danishefsky SJ (2000) J Org Chem 65:144
Ferrier RJ, Zubkov OA (2000) Org React submitted
Fischer E (1914) Chem Ber 47:196
Bergmann M (1925) Liebigs Ann Chem 443:223
Fraser-Reid B, Radatus B (1970) J Am Chem Soc 92:5288
Ferrier RJ, Overend WG, Ryan AE (1962) J Chem Soc 3667
Tejima S, Haga M, Nakamura H, Maki T, Sakata M, Agaki M (1963) Abstr Papers Am Chem Soc Meeting 145:7D
Bowles WA, Robins RA (1964) J Am Chem Soc 86:1252
Ferrier RJ (1964) J Chem Soc 5443
Brakta M, Lhoste P, Sinou D (1989) J Org Chem 54:1890
Doboszewski B, Blaton N, Herdewijn P (1995) J Org Chem 60:7909
Ogihara T, Mitsunobu O (1983) Tetrahedron Lett 24:3505
Leutzinger EE, Robins RK, Townsend LB (1970) Tetrahedron Lett 3751
Koreeda M, Houston TA, Shull BK, Klemke E, Tuinman RJ (1995) Synlett 90
Toshima K, Matsua G, Ishizuka T, Ushiki Y, Nakata M, Matsumura S (1998) J Org Chem 63:2307
Sobti A, Sulikowski GA (1994) Tetrahedron Lett 35:3661
López JC, Gómez AM, Valverde S, Fraser-Reid B (1995) J Org Chem 60:3851
Kjølberg O, Neumann K (1993) Acta Chem Scand 47:843
Toshima K, Ishizuka T, Matsuo G, Nakata M, Kinoshita M (1993) J Chem Soc Chem Commun 704
Toshima K, Ishizuka T, Matsuo G, Nakata M (1993) Chem Lett 2013
Florent J-C, Monneret C (1982) Synthesis 29
Bhaté P, Horton D, Priebe W (1985) Carbohydr Res 144:331
Dunkerton LV, Adair NK, Euske JM, Brady KT, Robinson PD (1988) J Org Chem 53:845
Descotes G, Martin J-C (1977) Carbohydr Res 56:168
(a) Byerley ALJ, Kenwright AM, Steel PG (1996) Tetrahedron Lett 37:9093; (b) Byerley ALJ, Kenwright AM, Steel PG (1997) ibid 38:2195; (c) Byerley ALJ, Kenwright AM, Lehmann CW, MacBride JAH, Steel PG (1998) J Org Chem 63:193
Dunkerton LV, Brady KT, Mohamed F, McKillican BP (1998) J Carbohydr Chem 7:49
(a) Daves GD (1990) Acc Chem Res 23:201; (b) Daves GD, Hallberg A (1989) Chem Rev 89:1433
Yougai S, Miwa T (1983) J Chem Soc Chem Commun 68
Basson MM, Holzapfel CW, Verdoorn GH (1998) Heterocycles 29:2261
Arai I, Daves GD (1981) J Am Chem Soc 103:7683
(a) Czernecki S, Dechavanne V (1983) Can J Chem 61:533; (b) Bellosta V, Czernecki S, Avenel D, Bahij SE, Gillier-Pandraud H (1990) ibid 68:1364
Takeda K, Nakamura H, Ayabe A, Akiyama A, Harigaya Y, Mizuno Y (1994) Tetrahedron Lett 35:125
Curran DP, Suh Y-G (1987) Carbohydr Res 171:161
(a) Hicks DR, Fraser-Reid B (1975) Can J Chem 53:2017; (b) Rajanbabu TV (1985) J Org Chem 50:3642
Grynkiewicz G, Priebe W, Zamojski A (1979) Carbohydr Res 68:33
Ciment DM, Ferrier RJ (1966) J Chem Soc (C) 441
Ferrier RJ, Ilanko G unpublished results
Danishefsky SJ, Kerwin JF (1982) J Org Chem 47:3803
Herscovici J, Muleka K, Boumaîza L, Antonakis K (1990) J Chem Soc Perkin Trans 1 1995
De las Heras FG, San Felix A, Fernández-Resa P (1983) Tetrahedron 39:1617
Grynkiewicz G, BeMiller JN (1982) Carbohydr Res 108:229
Tulshian DB, Fraser-Reid B (1984) J Org Chem 49:518
Dawe RD, Fraser-Reid B (1981) J Chem Soc Chem Commun 1180
Casiraghi G, Cornia M, Colombo L, Rassu G, Fava GG, Belicchi MF, Zetta L (1988) Tetrahedron Lett 29:5549
(a) Tam SY-K, Fraser-Reid B (1975) Carbohydr Res 45:29; (b) Madaj J, Rak J, Sokolowski J, Wisniewski A (1996) J Org Chem 61:2988
Gonzalez F, Lesage S, Perlin AS (1975) Carbohydr Res 42:267
Fehlhaber H-W, Snatzke G, Vlahov I (1987) Liebigs Ann Chem 637
Mostowicz D, Jurczak M, Hamann H-J, Hoft E, Chmielewski M (1998) Eur J Org Chem 2617
Jarglis P, Lichtenthaler FW (1982) Tetrahedron Lett 23:3781
Ferrier RJ, Prasad N (1969) J Chem Soc (C) 581
Inaba K, Matsumura S, Yoshikawa S (1991) Chem Lett 485
Guthrie RD, Irvine RW, Davison BE, Henrick K, Trotter J (1981) J Chem Soc Perkin Trans 2 468
Frappa I, Sinou D (1995) Synth Commun 25 2941
Noshita T, Sugiyama T, Kitazumi Y, Oritani T (1995) Biosci Biotech Biochem 59:2052
Sobti A, Sulikowski GA (1994) Tetrahedron Lett 35:3661
Ferrier RJ, Prasad N (1969) J Chem Soc (C) 570
Canas-Rodriguez A, Martinez-Tobed A (1979) Carbohydr Res 68:43
Wieczorek E, Thiem J (1998) Carbohydr Res 307:263
Canas-Rodriguez A, Ruiz-Poveda SG, Coronel-Borges LA (1987) Carbohydr Res 159:217
Klaffke W, Pudlo P, Springer D, Thiem J (1991) Liebigs Ann Chem 509
Banik BK, Manhas MS, Bose AK (1994) J Org Chem 59:4714
Deshpande PP, Price KN, Baker DC (1996) J Org Chem 61:455
Nicolaou KC, Hwang C-K, Duggan ME (1986) J Chem Soc Chem Commun 925
(a) Dorgan BJ, Jackson RFW (1996) Synlett: 859; (b) Orsini F, Pelizzoni F (1993) Carbohydr Res 243:183; (c) Thorn SN, Gallagher T (1996) Synlett 185
Thorn SN, Gallagher T (1996) Synlett 856
(a) Ichikawa Y, Isobe M, Goto T (1984) Tetrahedron Lett 25:5049; (b) Wincott FE, Danishefsky SJ, Schulte G (1987) ibid 28:4951; (c) Nicolaou KC, Duggan ME, Hwang C-K (1989) J Am Chem Soc 111:6666
de Raadt A, Stütz AE (1991) Carbohydr Res 220:101
Tsukiyama T, Isobe M (1992) Tetrahedron Lett 33:7911
Tsukiyama T, Peters SC, Isobe M (1993) Synlett 413
Grynkiewicz G, BeMiller JN (1982) J Carbohydr Chem 1:121
Dawe RD, Fraser-Reid B (1984) J Org Chem 49:522
Ramesh NG, Balasubramanian KK (1992) Tetrahedron Lett 33:3061
(a) Casiraghi G, Cornia M, Rassu G, Zetta L, Fava GG, Belicchi MF (1988) Tetrahedron Lett 29:3323; (b) Casiraghi G, Cornia M, Rassu G, Zetta L, Fava GG, Belicchi MF (1989) Carbohydr Res 191:243
Herscovici J, Delatre S, Antonakis K (1987) J Org Chem 52:5691
Priebe W, Zamojski A (1980) Tetrahedron 36:287
(a) Wittman MD, Halcomb RL, Danishefsky SJ, Golik J, Vyas D (1990) J Org Chem 55: 1979; (b) de Raadt A, Ferrier RJ (1991) Carbohydr Res 216:93
Brown DS, Bruno M, Davenport RJ, Ley SV (1989) Tetrahedron 45:4293
Guthrie RD, Irvine RW (1980) Carbohydr Res 82:207
Ferrier RJ, Ponpipom MM (1971) J Chem Soc (C) 553
De las Heras FG, Stud M (1977) Tetrahedron 33:1513
Doboszewski B, Blaton R, Herdewijn P (1995) Tetrahedron Lett 36:1321
Bessodes M, Egron M-J, Filippi J, Antonakis K (1990) J Chem Soc Perkin Trans 1 3035
Kondo T, Nakai H, Goto T (1973) Tetrahedron 29:1801
Bock K, Pedersen C (1970) Acta Chem Scand 24:2465
Bock K, Pedersen C (1969) Tetrahedron Lett: 2983
Macdonald SJF, McKenzie TC (1988) Tetrahedron Lett 29:1363
Paulsen H, Thiem J (1973) Chem Ber 106:3850
Alexander P, Krishnamurthy VV, Prisbe EJ (1996) J Med Chem 39:1321
Grynkiewicz G (1984) Carbohydr Res 128:C9
Ferrier RJ, Prasad N, Sankey G H (1968) J Chem Soc (C) 974
Köll P, Klenke K, Eiserman D (1984) J Carbohydr Chem 3:403
Thiem J, Schwentner J, Schüttpelz E, Kopf J (1979) Chem Ber 112:1023
Ferrier RJ, Prasad N, Sankey GH (1969) J Chem Soc (C) 587
(a) Onodera K, Yajima T (1970) Carbohydr Res 13:97; (b) Ferrier RJ, Ponpipom MM (1971) J Chem Soc (C) 560
Bock K, Pedersen C (1971) Acta Chem Scand 25:1021
Booma C, Balasubramanian KK (1992) Tetrahedron Lett 33:3049
Armstrong PL, Coull IC, Hewson AT, Slater MJ (1995) Tetrahedron Lett 36:4311
(a) Mereyala HB, Venkataramanaiah KC, Dalvoy VS (1992) Carbohydr Res 225:151; (b) Lauer G, Oberdorfer F (1993) Angew Chem Int Ed Engl 32:272; (c) Sharma GVM, Ramanaiah KCV, Krishnudu K (1994) Tetrahedron Asymmetry 5:1905
Gomez AM, Valverde S, Fraser-Reid B (1991) J Chem Soc Chem Commun 1207
Guthrie RD, Irvine RW (1980) Carbohydr Res 82:225
Ireland RE, Daub JP (1981) J Org Chem 46:479
Bertrand P, Gesson J-P, Renoux B, Tranoy I (1995) Tetrahedron Lett 36:4073
Paquette LA, Kinney MJ, Dullweber U (1997) J Org Chem 62:1713
Booma C, Balasubramanian KK (1993) Tetrahedron Lett 34:6757
Okabe M, Sun R-C (1989) Tetrahedron Lett 30:2203
Tam SY-K, Fraser-Reid B (1977) Can J Chem 55:3996
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Ferrier, R.J. (2001). Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives. In: Stütz, A.E. (eds) Glycoscience. Topics in Current Chemistry, vol 215. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-44422-X_7
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