Sugars as chiral auxiliaries

The Organic Chemistry of Sugars

Volumn , Issue , 2005, Pages 427-488

  Pleuss, Norbert ^a   Zech, Gernot ^a   Furman, Bartlomiej ^b   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548423526     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420027952     Document Type: Chapter

References (185)

1. Fischer, E, Verbindungen des Phenylhydrazins mit den Zuckerarten, Ber. Dtsch. Chem. Ges., 17, 579-588, 1884.
2. Landsteiner, K, Wiener. Klin. Wochenschrift, 14, 1132, 1901.
3. Somers, W T, Tang, J, Shaw, G D, Camphausen, R T, Insights into the molecular basis of leukocyte tethering and rolling revealed by structures of P-and E-selectin bound S Le(x) and PSGL-1, Cell., 103, 467-479, 2000, and references cited therein.
4. Fukuda, M, Tsuboi, S, Mucin-type O-glycans and leukosialin, Biochim. Biophys. Acta, 1455, 205-217, 1999, and references cited therein.
5. Ernst, B, Hart, G W, Sinaÿ, P, Carbohydrates in Chemistry and Biology, Vol. 1, Wiley-VCH, Weinheim, 2000.
6. Vankar, Y D, Schmidt, R R, Chemistry of glycosphingolipids-carbohydrate molecules of biological significance, Chem. Soc. Rev., 29, 201-216, 2000.
7. Herzner, H, Reipen, T, Schultz, M, Kunz, H, Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs, Chem. Rev., 100, 4495-4537, 2000.
8. Hollingsworth, R I, Wang, G, Towards a carbohydrate-based chemistry: progress in the development of general-purpose chiral synthons from carbohydrates, Chem. Rev., 100, 4267-4282, 2000.
9. Rueck, K, Kunz, H, Carbohydrates as chiral auxiliaries in stereoselective synthesis, Angew. Chem. Int. Ed., 32, 336-358, 1993.
10. Hultin, P G, Earle, M A, Sudharshan, M, Synthetic studies with carbohydrate-derived chiral auxiliaries, Tetrahedron, 53, 14823-14870, 1997.
11. Naumann, K, Synthetic Pyrethroid Insecticides: Structure and Properties, Springer, Berlin, 1990.
12. Reissig, H U, The Chemistry of the Cyclopropyl Group. Part 1, Wiley, Chichester, 1987.
13. Reissig, H U, Formation of C-C bonds by [2 þ1] cycloadditions, In Methods of Organic Chemistry (Houben-Weyl), Vol. 21c, Helmchen, G, Hoffmann, R W, Mulzer, J, Schaumann, E, Eds., Thieme, Stuttgart, pp. 3179-3270, 1995.
14. Murali, R, Ramana, C V, Nagarajan, N, Synthesis of 1,2-cyclopropanated sugars from glycals, J. Chem. Soc. Chem. Commun., 217-218, 1995.
15. Charette, A B, Coté, B, Marcoux, J F, Carbohydrates as chiral auxiliaries: asymmetric cyclopropanation reaction of acyclic olefins, J. Am. Chem. Soc., 113, 8166-8167, 1991.
16. Charette, A B, Turcotte, N, Marcoux, J F, The use of a-D-glucopyranosides as surrogates for the b-Lglucopyranosides in the stereoselective cyclopropanation reaction, Tetrahedron Lett., 35, 513-516, 1994.
17. Charette, A B, Coté, B, Stereoselective synthesis of all four isomers of coronamic acid: a general approach to 3-methanoamino acids, J. Am. Chem. Soc., 117, 12721-12732, 1995.
18. Kang, J, Lim, G J, Yoon, S K, Kim, M Y, Asymmetric cyclopropanation using new chiral auxiliaries derived from D-fructose, J. Org. Chem., 60, 564-577, 1995.
19. Schumacher, R, Reissig, H U, Stereoselective cyclopropanation of chiral carbohydrate-derived enol ethers, Synlett, 1121-1122, 1996.
20. Mattay, J, Conrads, R, Hoffmann, R, Formation of C-C bonds by light-induced [2 þ2] cycloadditions, In Methods of Organic Chemistry (Houben-Weyl), Vol. 21c, Helmchen, G, Hoffmann, R W, Mulzer, J, Schaumann, E, Eds., Thieme, Stuttgart, pp. 3085-3178, 1995.
21. Carless, H A J, Photochemistry in Organic Synthesis, Spec. Publ. No. 57, Royal Society of Chemistry, London, 1986.
22. Jarosz, S, Zamojski, A, Asymmetric photocycloaddition between furan and optically active ketones, Tetrahedron, 38, 1453-1456, 1982.
23. Pelzer, R, Juetten, P, Scharf, H D, Isoselektivität bei der asymmetrischen Paterno-Buechi-Reaktion unter Verwendung von Kohlenhydraten als chirale Auxiliare, Chem. Ber., 122, 487-491, 1989.
24. Woodward, R B, Hoffmann, R, The Conservation of Orbital Symmetry, Academic, New York, 1971.
25. Tidwell, T T, Ketenes, Wiley, New York, 1995, pp. 459-527.
26. Ganz, I, Kunz, H, Carbohydrates as chiral auxiliaries. [2 þ2] Cycloadditions to enol ethers, Synthesis, 1353-1357, 1994.
27. Georg, G I, Ravikumar, V T, In The Organic Chemistry of b-Lactams, Georg, G I, Ed., VCH Publishers, Inc., New York, pp. 295-381, 1993.
28. Thomas, R C, In Recent Progress in the Chemical Synthesis of Antibiotics, Lukacs, G, and Ohno, M, Eds., Springer, Berlin, pp. 533-562, 1990.
29. Cossio, F P, Arrieta, A, Lecea, B, Ugalde, J M, Chiral control in the Staudinger reaction between ketenes and imines. A theoretical SCF-MO study on asymmetric torquoselectivity, J. Am. Chem. Soc., 116, 2085-2093, 1994.
30. Borer, B C, Balogh, D W, An asymmetric synthesis of a 3-hydroxy-b-lactam by ketene-imine cycloaddition: utilization of chiral ketenes from carbohydrates, Tetrahedron Lett., 32, 1039-1040, 1991.
31. Saul, R, Kopf, J, Koell, P, Synthesis of a new chiral oxazolidinone auxiliary based on D-xylose and its application to the Staudinger reaction, Tetrahedron: Asymmetry, 11, 423-433, 2000.
32. Georg, G I, Akguen, E, Masheva, P M, Milstead, M, Ping, H, Wu, Z J, Velde, D V, Galactose-imines in the Staudinger reaction, Tetrahedron Lett., 33, 2111-2114, 1992.
33. Barton, D H R, Gateau-Oleska, A, Anaya-Mateos, J, Cléophax, J, Géro, S D, Chiaroni, A, Riche, C, Asymmetric synthesis of 1,3,4-trisubstituted and 3,4-disubstituted 2-azetidinones: strategy based on use of D-glucosamines as a chiral auxiliary in the Staudinger reaction, J. Chem. Soc. Perkin. Trans. 1, 3211-3212, 1990.
34. Dhar, D N, Murthy, K S M, Recent advances in the chemistry of chlorosulfonyl isocyanate, Synthesis, 437-449, 1986.
35. Effenberger, F, Kiefer, G, Stereochemistry of the cycloaddition of sulfonyl isocyanates and N-sulfinylsulfonamides to enol ethers, Angew. Chem. Int. Ed., 6, 951-952, 1967.
36. Cossio, F P, Roa, G, Lecea, B, Ugalde, J M, Substituent and solvent effect in the [2 þ2] cycloaddition reaction between olefins and isocyanates, J. Am. Chem. Soc., 117, 12306-12313, 1995.
37. Chmielewski, M, Kaluza, Z, Furman, B, Stereocontrolled synthesis of 1-oxabicyclic b-lactam antibiotics via [2 þ2] cycloaddition of isocyanates to sugar vinyl ethers, Chem. Commun., 2689-2696, 1996.
38. Kaluza, Z, Furman, B, Patel, M, Chmielewski, M, Asymmetric induction in [2 þ2] cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinyl-glycofuranoses, Tetrahedron: Asymmetry, 5, 2179-2186, 1994.
39. Kaluza, Z, Furman, B, Chmielewski, M, Asymmetric induction in [2 þ2] cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-5-O-vinyl-D-glycofuranoses, Tetrahedron: Asymmetry, 6, 1719-1730, 1995.
40. Cinquini, M, Cozzi, F, 1,3-Dipolar cycloadditions, In Methods of Organic Chemistry (Houben-Weyl), Vol. 21c, Helmchen, G, Hoffmann, R W, Mulzer, J, Schaumann, E, Eds., Thieme, Stuttgart, pp. 2953-2987, 1995.
41. Gothelf, K V, Jorgensen, K A, Asymmetric 1,3-dipolar cycloaddition reactions, Chem. Rev., 98, 863-909, 1998.
42. Vasella, A, Synthese und Umwandlungen von Isoxazolidin-Nucleosiden, Helv. Chim. Acta, 60, 426-446, 1977.
43. Vasella, A, Stereoselektivität und Reaktivität bei der 1,3-dipolaren Cycloaddition chiraler N-(Alkoxyalkyl)nitrone, Helv. Chim. Acta, 60, 1273-1294, 1977.
44. Huber, R, Vasella, A, The kinetic anomeric effect. Additions of nucleophiles and of dipolarophiles to N-glycosylnitrones and to N-pseudoglycosylnitrones, Tetrahedron, 46, 33-58, 1990.
45. Machetti, F, Cordero, F M, De Sarlo, F, Guarna, A, Brandi, A, A new synthesis of (2S)-4-oxopipecolic acid by thermal rearrangement of enantiopure spirocyclopropaneisoxazolidine, Tetrahedron Lett., 37, 4205-4208, 1996.
46. Kasahara, K, Iida, H, Kibayashi, Ch., Asymmetric total synthesis of (þ)-negamycin and (2)-3-epinegamycin via enantioselective 1,3-dipolar cycloaddition, J. Org. Chem., 54, 2225-2233, 1989.
47. Chiacchio, U, Corsaro, A, Gumina, G, Rescifina, A, Iannazzo, D, Piperno, A, Romeo, G, Romeo, R, Homochiral a-D-and b-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition, J. Org. Chem., 64, 9321-9327, 1999.
48. Mzengeza, S, Yang, C M, Whitney, R A, A total synthesis of acivicin, J. Am. Chem. Soc., 109, 276-277, 1987.
49. Fisera, L, Al-Timara, U A R, Ertl, P, Prónayová, N, Preparation and stereoselectivity of 1,3-dipolar cycloaddition of D-glucose-derived nitrones to N-arylmaleimides, Monatsh. Chem., 124, 1019-1029, 1993.
50. Yokoyama, M, Yamada, N, Togo, H, Synthesis of spiro sugar isoxazolidines via tandem Michael addition-1,3-dipolar cycloaddition, Chem. Lett., 753-756, 1990.
51. Tamura, O, Mita, N, Kusaka, N, Suzuki, H, Sakamoto, M, Intramolecular cycloaddition of a-allyloxycarbonylnitrone bearing a chiral sugar auxiliary: a short-step synthesis of the N-terminal amino acid component of nikkomycin Bz, Tetrahedron Lett., 38, 428-432, 1997.
52. 2-isoxazolines via addition of nitrile oxides to chiral acryloyl esters bearing cyclitols as auxiliaries, Tetrahedron Lett., 33, 5763-5766, 1992.
53. Ao, Z, Ying, K, Biao, J, Asymmetric 1,3-dipolar cycloaddition of nitrile oxides to chiral acryloyl esters bearing glucofuranose as auxiliary, Chin. J. Chem., 18, 220-224, 2000.
54. Oppolzer, W, Intermolecular Diels-Alder reactions, In Comprehensive Organic Synthesis, Trost, B M, Fleming, I, Paquette, L A, Eds., Pergamon Press, Oxford, pp. 315-399, 1991.
55. Tietze, L F, Kettschau, G, Hetero-Diels-Alder reactions in organic chemistry, In Topics in Current Chemistry: Stereoselective Heterocyclic Synthesis I, Metz, P, Ed., Springer, Berlin, pp. 1-120, 1997.
56. Helmchen, G, Hoffmann, R W, Mulzer, J, Schaumann, E, Eds., [4 þ2] cycloadditions (Chapter 1.6), In Methods of Organic Chemistry (Houben-Weyl), Vol. 21c, Thieme, Stuttgart, 1995.
57. Rueck-Braun, K, Kunz, H, Chiral Auxiliaries in Cycloadditions, Wiley-VCH, Weinheim, 1999.
58. David, S, Eustache, J, Lubineau, A, Cycloaddition as a possible path to disaccharide synthesis: stereochemical course of the reaction of butyl glyoxylate with a chiral, protected dienyl ether of glucose, J. Chem. Soc. Perkin. Trans. 1, 2274-2278, 1974.
59. David, S, Lubineau, A, Thieffry, A, Stéréochimie de la cycloaddition sur les éthers butadiényliques d’alcools chiraux. Dérivés en 4 et 6 de glucosides perbenzylés, Tetrahedron, 34, 299-304, 1978.
60. Kunz, H, Mueller, B, Schanzenbach, D, Diastereoselective Diels-Alder reactions using carbohydrate templates, Angew. Chem. Int. Ed., 26, 267-269, 1987.
61. Staehle, W, Kunz, H, Carbohydrates as chiral templates: stereoselective Diels-Alder synthesis with dienes of differing reactivity, Synlett, 260-262, 1991.
62. Gras, J L, Poncet, A, Nouguier, R, Ligand assisted asymmetric synthesis. II. Diastereoselective Diels-Alder additions with Lewis acid attracting auxiliaries derived from pentitols, Tetrahedron Lett., 33, 3323-3326, 1992.
63. Nouguier, R, Gras, J L, Giraud, B, Virgili, A, Methyl 3,4-b-D-arabinoside as a new chiral template for the asymmetric Diels-Alder reaction, Tetrahedron Lett., 32, 5529-5530, 1991.
64. Nouguier, R, Gras, J L, Giraud, B, Virgili, A, Induction asymétrique dans la réaction de Diels-Alder du cyclopentadiène sur des dérivés acryliques de O-méthylèneacétals de l’arabinose et du ribose, Tetrahedron, 48, 6245-6252, 1992.
65. Nouguier, R, Mignon, V, Gras, J L, Synthesis of methylene acetals in the D-glucose, D-galactose, Dmannose, and D-fructose series by an improved transacetalation reaction from dimethoxymethane, Carbohydr. Res., 277, 339-345, 1995.
66. Nouguier, R, Mignon, V, Gras, J L, Synthesis of enantiomerically pure (2S)-2-endo-hydroxymethyl-5-norbornene by Diels-Alder reaction based on a new fructose-derived auxiliary, J. Org. Chem., 64, 1412-1414, 1999.
67. Shing, T K M, Chow, H F, Chung, I H F, Sugarometallic chemistry: aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction, Tetrahedron Lett., 37, 3713-3716, 1996.
68. Akiyama, T, Horiguchi, N, Ida, T, Ozaki, S, Stereodivergent Diels-Alder reactions employing cyclitols as chiral auxiliaries, Chem. Lett., 975-976, 1995.
69. Loupy, A, Monteux, D, Asymmetric Diels-Alder: monobenzylated isosorbide and isomannide as highly effective chiral auxiliaries, Tetrahedron Lett., 37, 7023-7026, 1996.
70. Ferreira, M L G, Pinheiro, S, Perrone, C C, Costa, P R R, Ferreira, V F, New carbohydrate-based auxiliaries in Diels-Alder reaction, Tetrahedron: Asymmetry, 9, 2671-2680, 1998.
71. Banks, M R, Blake, A J, Cadogan, J I G, Dawson, I M, Gaur, S, Gosney, I, Gould, R O, Grant, K J, Hodgson, P K G, (5R)-7,8,9,10-Di-O-isopropylidene-2,6-dioxa-4-azaspiro[4,5]-decan-3-one: a new chiral spirooxazolidin-2-one derived from D-(þ)-galactose for use in asymmetric tranformations, J. Chem. Soc. Chem. Commun., 1146-1148, 1993.
72. Banks, M R, Cadogan, J I G, Gosney, I, Gaur, S, Hodgson, P K G, Highly regio-and stereospecific preparation of a new carbohydrate-based 1,3-oxazin-2-one by the INIR method and its application in some asymmetric transformations, Tetrahedron: Asymmetry, 5, 2447-2458, 1994.
73. Banks, M R, Cadogan, J I G, Gosney, I, Gould, R O, Hodgson, P K G, McDougall, D, Preparation of enantiomerically pure fructose-derived 1,3-oxazin-2-one by INIR methodology and its application as a chiral auxiliary in some model asymmetric reactions, Tetrahedron, 54, 9765-9784, 1998.
74. Kunz, H and Engel, S, Unpublished results.
75. Engel, S, PhD dissertation, University of Mainz, 1994.
76. Horton, D, Koh, D, Generalized approach from sugars to enantiomerically pure tetra-C-substituted carbocycles, Tetrahedron Lett., 34, 2283-2286, 1993.
77. Horton, D, Koh, D, Takagi, Y, Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: reactivities of cis-dienophiles with cyclopentadiene, Carbohydr. Res., 250, 261-274, 1993.
78. Horton, D, Koh, D, Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: reactivities of acyclic seven-carbon trans-dienophiles derived from aldopentoses, Carbohydr. Res., 250, 249-260, 1993.
79. Serrano, J A, Moreno, M C, Román, E, Arjona, O, Plumet, J, Jimenéz, J, Enantioselective synthesis of cyclohexene nitro aldehydes via Diels-Alder reactions with sugar nitroolefins, J. Chem. Soc. Perkin. Trans 1, 3207-3212, 1991.
80. Serrano, J A, Cáceres, L E, Román, E, Asymmetric Diels-Alder reactions of chiral sugar nitroalkene: diastereofacial selectivity and regioselectivity, J. Chem. Soc. Perkin. Trans, 1, 941-942, 1992.
81. Serrano, J A, Cáceres, L E, Román, E, Asymmetric Diels-Alder reactions between chiral sugar nitroalkenes and 1-O-substituted buta-1,3-dienes. Synthesis and reactivity of new cyclohexenyl derivatives, J. Chem. Soc. Perkin. Trans 1, 1863-1871, 1995.
82. Franck, R W, Argade, S, Subramanian, C S, Frechet, D M, The face selectivity directed by an allylic group of a diene in the Diels-Alder reaction is reversed from that of a dienophile, Tetrahedron Lett., 26, 3187-3190, 1985.
83. Kahn, S D, Hehre, W J, Modeling chemical reactivity. 5. Facial selectivity in Diels-Alder cycloadditions, J. Am. Chem. Soc., 109, 663-666, 1987.
84. Gupta, R C, Raynor, C M, Stoodley, R J, Slawin, A M Z, Williams, D J, Asymmetric Diels-Alder reactions. Part 1. Diastereofacial reactivity of (E)-3-trimethylsilyloxybuta-1,3-dienyl 2,3,4,6-tetra-Oacetyl-b-D-glucopyranoside towards cyclic dienophiles, J. Chem. Soc. Perkin. Trans 1, 1773-1785, 1988.
85. Gupta, R C, Larsen, D S, Stoodley, R J, Slawin, A M Z, Williams, D J, Asymmetric Diels-Alder reactions. Part 2. A model to account for the diastereofacial reactivity of (E)-1-(20,30,40,60-tetra-Oacetyl-b-D-glucopyranosyloxy)-3-trimethylsiloxybuta-1,3-diene and its 2-methyl derivative, J. Chem. Soc. Perkin. Trans 1, 739-749, 1989.
86. Beagley, B, Curtis, A D M, Pritchard, R G, Stoodley, R J, Asymmetric Diels-Alder reactions. Part 6. Regio-and stereo-selective cycloadditions of 5-020,30,40,60-tetra-O-acetyl-b-D-glucopyranosyloxy)-1, 4-naphthoquinone, J. Chem. Soc. Perkin. Trans 1, 1981-1991, 1992.
87. Pornpakakul, S, Pritchard, R G, Stoodley, R J, Asymmetric synthesis of (2)-4-epi-shikimic acid, Tetrahedron Lett., 41, 2691-2694, 2000.
88. Ehlenz, R, Neuss, O, Teckenbrock, M, Doetz, K H, Carbohydrate functionalized oxacyclopentylidene complexes, Tetrahedron, 53, 5143-5158, 1997.
89. Doetz, K H, Ehlenz, R, Carbohydrate-modified metal carbenes: synthesis and first applications, Chem. Eur. J., 3, 1751-1756, 1997.
90. Weyershausen, B, Nieger, M, Doetz, K H, Chiral 2-oxacyclopentylidene complexes via metalassisted cycloisomerization of carbohydrate-derived butynols, Organometallics, 17, 1602-1707, 1998.
91. Weyershausen, B, Nieger, M, Doetz, K H, Stereospecific exo-selective Diels-Alder reactions with carbohydrate-functionalized a-exo-methylene-2-oxacyclopentylidene chromium complexes, J. Org. Chem., 64, 4206-4210, 1999.
92. Felber, H, Kresze, G, Prewo, R, Vasella, A, Diastereoselectivity and reactivity in the Diels-Alder reactions of a-chloronitroso ethers, Helv. Chim. Acta, 69, 1137-1146, 1986.
93. Werbitzky, O, Klier, K, Felber, H, Asymmetric induction of four chiral centres by hetero Diels-Alder reaction of a chiral nitroso dienophile, Liebigs Ann. Chem., 267-270, 1990.
94. Braun, H, Felber, H, Kresze, G, Schmidtchen, F P, Prewo, R, Vasella, A, Diastereoselektive Diels-Alder-Reaktionen mit a-Chloronitrososacchariden, Liebigs Ann. Chem., 261-268, 1993.
95. Zhang, D, Sueling, C, Miller, M J, The hetero Diels-Alder reactions between D-mannosederived halonitroso compounds and cyclopentadiene: scope and limitations, J. Org. Chem., 63, 885-888, 1998.
96. Arnold, T, Orschel, B, Reissig, H U, Diacetoneglucose as auxiliary group for the asymmetric hetero-Diels-Alder reaction with nitrosoalkenes, Angew. Chem. Int. Ed., 31, 1033-1035, 1992.
97. Schade, W, Reissig, H U, A new diastereoselective synthesis of enantiomerically pure 1,2-oxazines derivatives by addition of lithiated methoxyallene to chiral nitrones, Synlett, 632-634, 1999.
98. Pulz, R, Watanabe, T, Schade, W, Reissig, H U, A stereoconvergent synthesis of enantiopure 3-methoxypyrrolidines and 3-methoxy-2,5-dihydropyrroles from 3,6-dihydro-2H-1,2-oxazines, Synlett, 983-986, 2000.
99. Denmark, S E, Thorarensen, A, Tandem [4 þ2]/[3 þ2] cycloadditions of nitroalkenes, Chem. Rev., 96, 137-165, 1996.
100. Avalos, M, Babiano, R, Cintas, P, Higes, F J, Jiménez, J L, Palacios, J C, Silva, M A, Substratecontrolled stereodifferentiation of tandem [4 þ2]/[3 þ2] cycloadditions by a vicinal carbohydratebased template, J. Org. Chem., 61, 1880-1882, 1996.
101. Avalos, M, Babiano, R, Cintas, P, Jiménez, J L, Palacios, J C, Silva, M A, Asymmetric tandem reactions based on nitroalkenes: a one-pot construction of functionalized chiral bicycles by a threecomponent reaction, Chem. Commun., 459-460, 1998.
102. Avalos, M, Babiano, R, Cintas, P, Higes, F J, Jiménez, J L, Palacios, J C, Silva, M A, Diastereoselective cycloadditions of nitroalkenes as an approach to the assembly of bicyclic nitrogen heterocycles, J. Org. Chem., 64, 1494-1502, 1999.
103. Avalos, M, Babiano, R, Bravo, J L, Cintas, P, Jiménez, J L, Palacios, J C, Silva, M A, Understanding diastereofacial selection in carbohydrate-based domino cycloadditions: Semiempirical and DFT calculations, Chem. Eur. J., 6, 267-277, 2000.
104. Pfrengle, W, Kunz, H, Hetero Diels-Alder reactions on a carbohydrate template: stereoselective synthesis of (S)-anabasine, J. Org. Chem., 54, 4261-4263, 1989.
105. Aspinall, I H, Cowley, P M, Mitchell, G, Stoodley, R J, Asymmetric synthesis of (3S)-2,3,4,5-tetrahydropyridazine-3-carboxylic acid, J. Chem. Soc. Chem. Commun., 1179-1180, 1993.
106. Aspinall, I H, Cowley, P M, Stoodley, R J, Enhanced discrimination by aza dienophiles over their olefinic counterparts for the diastereotopic faces of methyl (E, E)-5-(20,30.40,60-tetra-O-acetyl-b-Dglucopyranosyloxy) penta-2,4-dienoate, Tetrahedron Lett., 35, 3397-3400, 1994.
107. Avalos, M, Babiano, R, Cintas, P, Clemente, F R, Jiménez, J L, Palacios, J C, Sánchez, J B, Hetero Diels-Alder reactions of homochiral 1,2-diaza-1,3-butadienes with diethyl azodicarboxylate under microwave irradiation. Theoretical rationale of the stereochemical outcome, J. Org. Chem., 64, 6297-6305, 1999.
108. McCarrick, M A, Wu, Y D, Houk, K N, Hetero Diels-Alder reaction transition structures: reactivity, stereoselectivity, catalysis, solvent effects and the exo-lone-pair effect, J. Org. Chem., 58, 3330-3343, 1993.
109. Lowe, R F, Stoodley, R J, Hetero Diels-Alder reaction involving (E)-3-(tert-butyldimethylsiloxy)-1-(20,30,40,60-tetra-O-acetyl-b-D-glucopyranosyloxy)buta-1,3-diene and p-nitrobenzaldehyde, Tetrahedron Lett., 35, 6351-6354, 1994.
110. Cousins, R P C, Curtis, A D M, Ding, W C, Stoodley, R J, 1,5-Asymmetric inductions in the reactions of 2-(20,30,40,60-tetra-O-acetyl-b-D-glucopyranosyloxy)benzaldehyde with Danishefsky’s diene, Tetrahedron Lett., 36, 8689-8692, 1995.
111. Bednarski, M, Danishefsky, S, On the interactivity of chiral auxiliaries with chiral catalysts in the hetero Diels-Alder reaction: a new route to L-glycolipids, J. Am. Chem. Soc., 105, 6968-6969, 1983.
112. Bednarski, M, Danishefsky, S, Interactivity of chiral catalysts and chiral auxiliaries in the cycloaddition of activated dienes with aldehydes: a synthesis of L-glucose, J. Am. Chem. Soc., 108, 7060-7067, 1986.
113. Kunz, H, Stereoselective syntheses using carbohydrates as chiral auxiliaries, Pure Appl. Chem., 67, 1627-1635, 1995.
114. Kunz, H, Weymann, M, Follmann, M, Allef, P, Oertel, K, Schultz-Kukula, M, Hofmeister, A, Stereoselective syntheses of chiral heterocycles and alkaloids using carbohydrate auxiliaries, Polish J. Chem., 73, 15-27, 1999.
115. Kunz, H, Sager, W, Schanzenbach, D, Decker, M, Carbohydrates as chiral templates: stereoselective Strecker synthesis of D-a-amino nitriles and acids using O-pivaloylated D-galactosylamine as the auxiliary, Liebigs Ann. Chem., 649-654, 1991.
116. Kunz, H, Sager, W, Diastereoselective Strecker synthesis of a-amino nitriles using carbohydrate templates, Angew. Chem. Int. Ed., 26, 557-559, 1987.
117. Kunz, H, Pfrengle, W, Asymmetric synthesis on carbohydrate templates: stereoselective Ugi synthesis of a-amino acid derivatives, J. Am. Chem. Soc., 110, 651-652, 1988.
118. Kunz, H, Pfrengle, W, Carbohydrates as chiral templates: asymmetric Ugi-synthesis of a-amino acids using galactosylamines as the chiral matrices, Tetrahedron, 44, 5487-5494, 1988.
119. Kunz, H, Pfrengle, W, Sager, W, Carbohydrates as chiral templates: diastereoselective Ugi synthesis of (S)-amino acids using O-acylated D-arabinopyranosylamine as the auxiliary, Tetrahedron Lett., 30, 4109-4110, 1989.
120. Goebel, M, Ugi, I, O-Alkyl-D-glucopyranosylamines and their derivatives, Synthesis, 1095-1098, 1991.
121. Lehnhoff, S, Goebel, M, Karl, R M, Kloesel, R, Ugi, I, Stereoselective syntheses of peptide derivatives with 2-acetamido-3,4,6-tri-O-acetyl-1-amino-2-deoxy-b-D-glucopyranose by 4-component condensation, Angew. Chem. Int. Ed., 34, 1104-1107, 1995.
122. Linderman, R J, Binet, S, Petrich, S R, Enhanced diastereoselectivity in the asymmetric Ugi reaction using a new “convertible” isonitrile, J. Org. Chem., 64, 336-337, 1999.
123. Oertel, K, Zech, G, Kunz, H, Stereoselective combinatorial Ugi-multicomponent synthesis on solid phase, Angew. Chem. Int. Ed., 39, 1431-1433, 2000.
124. Ziegler, T, Schloemer, R, Koch, C, Passerini and Ugi reactions of anomeric glucosyl isonitriles, Tetrahedron Lett., 39, 5957-5960, 1998.
125. Ziegler, T, Kaisers, H J, Schloemer, R, Koch, C, Passerini and Ugi reactions of benzyl and acetyl protected isocyanoglucoses, Tetrahedron, 55, 8397-8408, 1999.
126. Lockhoff, O, An access to glycoconjugate libraries through multicomponent reactions, Angew. Chem. Int. Ed., 37, 3436-3439, 1998.
127. Vincent, S P, Schleyer, A, Wong, C H, Asymmetric Strecker synthesis of C-glycopeptide, J. Org. Chem., 65, 4440-4443, 2000.
128. Schlemminger, I, Janknecht, H H, Maison, W, Saak, W, Martens, J, Synthesis of the first enantiomerically pure 3-thiazolines via Asinger reaction, Tetrahedron Lett., 41, 7289-7292, 2000.
129. Laschat, S, Kunz, H, Carbohydrates as chiral templates: Stereoselective synthesis of chiral homoallyl amines and b-amino acids, Synlett, 51-52, 1990.
130. Laschat, S, Kunz, H, Carbohydrates as chiral templates: diastereoselective synthesis of N-glycosyl-N-homoallylamines and b-amino acids from imines, J. Org. Chem., 56, 5883-5889, 1991.
131. Deloisy, S, Kunz, H, A novel synthesis of chain-extended amino sugar derivatives through Aza-Cope rearrangement of N-galactosyl-N-homoallylamines, Tetrahedron Lett., 39, 791-794, 1998.
132. Laschat, S, Kunz, H, Carbohydrates as chiral templates: stereoselective synthesis of (R)-and (S)-aaminophosphonic acid derivatives, Synthesis, 90-95, 1992.
133. Kunz, H, Schanzenbach, D, Carbohydrates as chiral templates: stereoselective synthesis of b-amino acids, Angew. Chem. Int. Ed., 28, 1068-1069, 1989.
134. Kunz, H, Burgard, A, Schanzenbach, D, Asymmetric syntheses of b-amino acids with two new stereogenic centres at the a and b-positions, Angew. Chem. Int. Ed., 36, 386-387, 1997.
135. Kunz, H, Pfrengle, W, Carbohydrates as chiral templates: stereoselective tandem Mannich-Michael reaction for the synthesis of piperidine alkaloids, Angew. Chem. Int. Ed., 28, 1067-1068, 1989.
136. Weymann, M, Pfrengle, W, Schollmeyer, D, Kunz, H, Enantioselective syntheses of 2-alkyl, 2,6-dialkylpiperidines and indolizidine alkaloids through diastereoselective Mannich-Michael reactions, Synthesis, 1151-1160, 1997.
137. Basha, A, Henry, R, McLaughlin, M A, Ratajczyk, J D, Wittenberger, S J, Addition of organometallic reagents to N-glycosyl nitrones. Enantioselective syntheses of (þ)-(R)-and (2)-(S)-zileuton, J. Org. Chem., 59, 6103-6106, 1994.
138. Rohloff, J C, Alfredson, T V, Schwartz, M A, Enantioselective synthesis of 5-LO inhibitors using a gulofuranose auxiliary, Tetrahedron Lett., 35, 1011-1014, 1994.
139. Stewart, A O, Bhatia, P A, Martin, J G, Summers, J B, Rodriques, K E, Martin, M B, Holms, J H, Moore, J L, Craig, R A, Kolasa, T, Ratajczyk, J D, Mazdiyasni, H, Kerdesky, F A J, DeNinno, S L, Maki, R G, Bouska, J B, Young, P R, Lanni, C, Bell, R L, Carter, G W, Brooks, C D W, Structure-activity relationships of N-hydroxyurea 5-lipoxygenase inhibitors, J. Med. Chem., 40, 1955-1968, 1997.
140. Young, R N, Inhibitors of 5-lipoxygenase: a therapeutic potential yet to be fully realized? Eur. J. Med. Chem., 34, 671-685, 1999.
141. Roush, W R, VanNieuwenhze, M S, [(Z)-g-[(Diisopropylidene-a-D-mannopyranosyl)oxy)allyl)-tributylstannane: a new chiral reagent for the asymmetric a-hydroxyallylation of aldehydes, J. Am. Chem. Soc., 116, 8536-8543, 1994.
142. Yamamoto, Y, Kobayashi, K, Okano, H, Kadota, I, Asymmetric synthesis of syn-1,2-diols via the reaction of aldehydes with chiral g-(tetrahydropyranyloxy)allylstannanes, J. Org. Chem., 57, 7003-7005, 1992.
143. Chika, J I, Takei, H, Arabinose as a chiral auxiliary for the asymmetric a-hydroxyallylation of aldehydes to syn-1,2-diols, Tetrahedron Lett., 39, 605-608, 1998.
144. Felix, D, Szymoniak, J, Moïse, C, Asymmetric allylation of aldehydes using tiglyltitanocenes attached to a carbohydrate, Tetrahedron, 53, 16097-16106, 1997.
145. Yoshida, T, Chika, J I, Takei, H, Asymmetric nucleophilic addition to b-and g-alkoxy aldehydes using carbohydrate as a chiral auxiliary, Tetrahedron Lett., 39, 4305-4308, 1998.
146. Shing, T K M, Li, L H, Asymmetric Hosomi-Sakurai reaction of allylsilanes containing arabinosederived alcohols as chiral auxiliaries, J. Org. Chem., 62, 1230-1233, 1997.
147. Rueck, K, Kunz, H, Stereoselective conjugate addition of organoaluminum chlorides to a, bunsaturated carboxylic acid derivatives, Synthesis, 1018-1028, 1993.
148. Rueck-Braun, K, Stamm, A, Engel, S, Kunz, H, b-branched a-halo carboxylic acid derivatives via stereoselective 1,4-addition of dialkylaluminum chlorides to a, b-unsaturated N-acyloxazolidinones, J. Org. Chem., 62, 967-975, 1997.
149. Totani, K, Nagatsuka, T, Yamaguchi, S, Takao, K, Ohba, S, Tadano, K, Highly diastereoselective 1, 4-addition of an organocuprate to methyl a-D-gluco, a-D-manno, or a-D-galactopyranosides tethering an a, b-unsaturated ester, J. Org. Chem., 66, 5965-5975, 2001.
150. Weymann, M, Schultz-Kukula, M, and Kunz, H, Auxiliary-controlled stereoselective enolate protonation: enantioselective synthesis of cis and trans annulated decahydroquinoline alkaloids, Tetrahedron Lett., 39, 7835-7838.
151. Comins, D L, Dehghani, A, A short, asymmetric synthesis of (2)-pumiliotoxin C, J. Chem. Soc. Chem. Commun., 1838-1839, 1993.
152. Heathcock, C H, White, C T, Morrison, J J, van Derveer, D, Double stereodifferentiation as a method for achieving superior Cram’s rule selectivity in aldol condensations with chiral aldehydes, J. Org. Chem., 46, 1296-1309, 1981.
153. Kunz, H, Mohr, J, Carbohydrates as chiral templates: reactivity and stereoselectivity of carboxylic ester enolates, J. Chem. Soc. Chem. Commun., 1315-1317, 1988.
154. Mulzer, J, Hiersemann, M, Buschmann, J, Luger, P, 1,2: 5,6-Di-O-isopropylidene-a-D-gulofuranose as a chiral auxiliary in the diastereoselective C-methylation of ester enolates, Liebigs Ann. Chem., 649-654, 1995.
155. Keynes, M N, Earle, M A, Sudharshan, M, Hultin, P G, Synthesis and asymmetric alkylation of glucose-derived bicyclic oxazinones, Tetrahedron, 52, 8685-8702, 1996.
156. Koell, P, Luetzen, A, D-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective alkylations, Tetrahedron: Asymmetry, 7, 637-640, 1996.
157. Angibaud, P, Chaumette, J L, Desmurs, J R, Duhamel, L, Ple, G, Valnot, J Y, Duhamel, P, Asymmetric synthesis of 2-chloro-and 2-bromo-alkanoic acids by halogenation of a-Dglucofuranose-derived silyl ketene acetals, Tetrahedron: Asymmetry, 6, 1919-1932, 1995.
158. Luetzen, A, Koell, P, D-Xylose derived oxazolidin-2-ones as chiral auxiliaries in stereoselective acylations and halogenations, Tetrahedron: Asymmetry, 8, 29-32, 1997.
159. Bandraege, S, Josephson, S, Moerch, L, Vallen, S, Asymmetric synthesis of b-hydroxyesters by Reformatsky reactions and amide base mediated condensations, Acta Chem. Scand. Ser. B, 35, 273-277, 1981.
160. Stoever, M, Luetzen, A, Koell, P, New glyco-oxazolidin-2-ones as chiral auxiliaries in boronmediated asymmetric aldol reactions, Tetrahedron: Asymmetry, 11, 371-374, 2000.
161. Evans, D A, Bartroli, J, Shih, T L, Enantioselective aldol condensations: erythro-selective chiral aldol condensations via boron-enolates, J. Am. Chem. Soc., 103, 2127-2129, 1981.
162. Akiyama, Y, Ishikawa, K, Ozaki, S, Asymmetric synthesis of functionalized tertiary alcohols by diastereoselective aldol reaction of silyl enol ether and ketene silyl acetals with a-keto esters bearing an optically active cyclitol as a chiral auxiliary, Synlett, 275-276, 1994.
163. Enders, D, Knopp, M, Schiffers, R, Asymmetric [3,3]-sigmatropic rearrangements in organic synthesis, Tetrahedron: Asymmetry, 7, 1847-1882, 1996.
164. Eguchi, T, Koudate, T, Kakinuma, K, The Overman-rearrangement on a diacetone-D-glucose template, Tetrahedron, 49, 4527-4540, 1993.
165. Tomooka, Y, Nakamura, Y, Nakai, T, [2,3]-Wittig-rearrangement using glucose as chiral auxiliary, Synlett, 321-322, 1995.
166. Harrington, P E, Tius, M A, Asymmetric cyclopentannelation-chiral auxiliary on the allene, Org. Lett., 2, 2447-2450, 2000.
167. Leonard, J, Diez-Barra, E, Merino, S, Control of asymmetry through conjugate addition reactions, Eur. J. Org. Chem., 2051-2061, 1998.
168. Murakata, M, Jono, T, Mizuno, Y, Hoshino, O, Construction of chiral quarternary carbon centers by catalytic enantioselective radical mediated allylation, J. Am. Chem. Soc., 119, 11713-11714, 1997.
169. Garner, P P, Cox, P B, Klippenstein, S J, Auxiliary induced r-stereocontrol in acetaloxyalkyl radical addition reactions, J. Am. Chem. Soc., 117, 4183-4184, 1995.
170. Barton, D H R, Crich, D, Kretzschmar, G, The invention of new radical chain reactions, part 9, J. Chem. Soc. Perkin. Trans. 1, 39-54, 1986.
171. Enholm, E J, Cottone, J S, Allais, F, Highly diastereoselective 5-hexenyl radical cyclizations with Lewis acids and carbohydrate scaffolds, Org. Lett., 3, 145-147, 2001.
172. Enholm, E J, Gallagher, M E, Jiang, S, Batson, W A, Free radical allyl transfers utilizing soluble noncross-linked polystyrene and carbohydrate scaffold supports, Org. Lett., 2, 3355-3357, 2000.
173. Mendonca, A J, Xiao, X Y, Optimization of solid supports for combinatorial chemical synthesis, Med. Res. Rev., 19, 451-462, 1999.
174. Sibi, M P, Chandramouli, S V, Intermolecular free radical reactions on solid support, allylation of esters, Tetrahedron Lett., 38, 8929-8932, 1997.
175. Enholm, E J, Gallagher, M E, Lombardi, J S, Moran, K M, Schulte, J P, An allylstannane reagent on non-cross-linked polystyrene support, Org. Lett., 1, 689-691, 1999.
176. Wentworth, P, Janda, K D, Liquid phase chemistry: recent advances in soluble polymer-supported catalysts, reagents and synthesis, Chem. Commun., 1917-1924, 1999.
177. Huang, G, Hollingsworth, R I, The stereoselective conversion of 2-alkenyl alcohols to (R)-or (S)-alkane-1,2-diols using D-glucose as chiral auxiliary, Tetrahedron Lett., 40, 581-584, 1999.
178. Nair, V, Prabhakaran, J, George, T G, A facile synthesis of optically active lactones using benzyl-3,6-anhydro glucofuranoside as chiral auxiliary, Tetrahedron, 44, 15061-15068, 1997.
179. Haan, J W, Son, S U, Chung, Y K, Chiral auxiliary directed asymmetric ortho-lithiation of (arene)tricarbonylchromium complexes, J. Org. Chem., 62, 8264-8267, 1997.
180. Duthaler, R O, Hafner, A, Riediker, M, Asymmetric C-C bond formation with titanium carbohydrate complexes, Pure Appl. Chem., 62, 631-642, 1990.
181. Allef, P, Kunz, H, Glycosylation-induced asymmetric synthesis: a-amino acid esters via Mannich reaction, Tetrahedron: Asymmetry, 11, 375-378, 2000.
182. Kumar, A, Oehme, G, Roque, J P, Schwarze, M, Selke, R, Increase in the enantioselectivity of asymmetric hydrogenation in water influenced by surfactants or polymerized micelles, Angew. Chem. Int. Ed., 33, 2197-2199, 1994.
183. RajanBabu, T V, Casalunovo, A L, Tailored ligands for asymmetric catalysis: the hydrocyanation of vinylarenes, J. Am. Chem. Soc., 114, 6265-6266, 1992.
184. Hamashima, Y, Kanai, M, Shibasaki, M, Catalytic enantioselective cyanosilylation of ketones, J. Am. Chem. Soc., 122, 7412-7413, 2000.
185. Glaeser, B, Kunz, H, Enantioselective allylic substitution using a novel (Phosphino-a-Dglucopyrano-oxazoline)-palladium catalyst, Synlett, 53-54, 1998.