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7944234138
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E. Fischer isolated DL-fructose and DL-sorbose as their phenylosazones, α-acrosazone and β-acrosazone, respectively. He derived these names from bromoacrolein (2,3-dibromopropionaldehyde), which upon treatment with base yields a product mixture that consists mainly of α- and β-acrose. The phenylosazones of these compounds were identical to those obtained by Fischer from formose. For Fischer's work, see, for example: a) E. Fischer, J. Tafel, Ber. Dtsch. Chem. Ges. 1887, 20, 1088-1094;
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Fischer, E.1
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14844284710
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reference [2b]
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For mechanistic considerations, see: a) reference [2b];
-
-
-
-
17
-
-
14844291634
-
-
note
-
It should be mentioned that formose consists mainly of pentoses, and that hexoses constitute only a small fraction of the mixture; see reference [2b].
-
-
-
-
18
-
-
84982342692
-
-
The observation that D-glyceraldehyde and 1,3-dihydroxyacetone (and even D-glyceraldehyde alone!) react in basic solution to yield D-fructose and D-sorbose as major products provided support for this pathway: H. O. L. Fischer, E. Baer, Helv. Chim. Acta 1936, 19, 519-532.
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M. Calvin, Angew. Chem. 1962, 74, 165-175; Angew. Chem. Int. Ed. Engl. 1962, 1, 65-75.
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M. Calvin, Angew. Chem. 1962, 74, 165-175; Angew. Chem. Int. Ed. Engl. 1962, 1, 65-75.
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For excellent reviews, see: a) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
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For excellent reviews, see: a) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1375;
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24
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0001676496
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For possible alternatives to DHAP, see: a) M. D. Bednarski, E. S. Simon, N. Bischofberger, W.-D. Fessner, M.-J. Kim, W. Lees, T. Saito, H. Waldmann, G. M. Whitesides, J. Am. Chem. Soc. 1989, 111, 627-635;
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25
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14844291739
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reference [11b]
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b) reference [11b];
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26
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0001674080
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c) DHA in the presence of inorganic arsenate can mimic DHAP: J. R. Durrwachter, D. G. Drueckhammer, K. Nozaki, H. M. Sweers, C.-H. Wong, J. Am. Chem. Soc. 1986, 108, 7812-7818; D. G. Drueckhammer, J. R. Durrwachter, R. L. Pederson, D. C. Crans, L. Daniels, C.-H. Wong, J. Org. Chem. 1989, 54, 70-77; R. Schoevaart, F. van Rantwijk, R. A. Sheldon, J. Org. Chem. 2001, 66, 4559-4562.
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27
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0001874707
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c) DHA in the presence of inorganic arsenate can mimic DHAP: J. R. Durrwachter, D. G. Drueckhammer, K. Nozaki, H. M. Sweers, C.-H. Wong, J. Am. Chem. Soc. 1986, 108, 7812-7818; D. G. Drueckhammer, J. R. Durrwachter, R. L. Pederson, D. C. Crans, L. Daniels, C.-H. Wong, J. Org. Chem. 1989, 54, 70-77; R. Schoevaart, F. van Rantwijk, R. A. Sheldon, J. Org. Chem. 2001, 66, 4559-4562.
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0035967772
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c) DHA in the presence of inorganic arsenate can mimic DHAP: J. R. Durrwachter, D. G. Drueckhammer, K. Nozaki, H. M. Sweers, C.-H. Wong, J. Am. Chem. Soc. 1986, 108, 7812-7818; D. G. Drueckhammer, J. R. Durrwachter, R. L. Pederson, D. C. Crans, L. Daniels, C.-H. Wong, J. Org. Chem. 1989, 54, 70-77; R. Schoevaart, F. van Rantwijk, R. A. Sheldon, J. Org. Chem. 2001, 66, 4559-4562.
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For the synthesis of sugars and their derivatives, see: a) C.-H. Wong, G. M. Whitesides, J. Org. Chem. 1983, 48, 3199-3205;
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c) reference [12c];
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d) J. R. Durrwachter, H. M. Sweers, K. Nozaki, C.-H. Wong, Tetrahedron Lett. 1986, 27, 1261-1264;
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For the synthesis of azasugars and their derivatives, see: a) T. Ziegler, A. Straub, F. Effenberger, Angew. Chem. 1988, 100, 737-738; Angew. Chem. Int. Ed. Engl. 1988, 27, 716-717;
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14844319359
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reference [32c]
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b) reference [32c].
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37049138119
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d) R. A. Y. Jones, A. R. Katritzky, K. A. F. Record, R. Scattergood, J. M. Sullivan, J. Chem. Soc. Perkin Trans. 2 1974, 402-406;
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86
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14844317440
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note
-
Majewski et al. developed another approach for the synthesis of 2,2-dimethyl-1,3-dioxan-5-one (33), similar to that depicted in Scheme 11 b. As the overall yields were lower and the synthesis was less amenable to scale-up, they finally prepared 33 according to the sequence shown in Scheme 11 b (see reference [35]).
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87
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0000129485
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M. Majewski, D. M. Gleave, P. Nowak, Can. J. Chem. 1995, 73, 1616-1626.
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a) For reviews, see: A. Job, C. F. Janeck, W. Bettray, R. Peters, D. Enders, Tetrahedron 2002, 58, 2253-2329;
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Job, A.1
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89
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0000434949
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(Ed.: J. D. Morrison), Academic Press, Orlando
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b) D. Enders in Asymmetric Synthesis, Vol. 3 (Ed.: J. D. Morrison), Academic Press, Orlando, 1984, pp. 275-339;
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Enders, D.1
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c) D. Enders, H. Kipphardt, P. Fey, Org. Synth. 1987, 65, 183-202;
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Enders, D.1
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d) D. Enders, H. Eichenauer, Angew. Chem. 1976, 88, 579-580; Angew. Chem. Int. Ed. Engl. 1976, 15, 549-550;
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Enders, D.1
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92
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d) D. Enders, H. Eichenauer, Angew. Chem. 1976, 88, 579-580; Angew. Chem. Int. Ed. Engl. 1976, 15, 549-550;
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94
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D. Enders, U. Jegelka, B. Dücker, Angew. Chem. 1993, 105, 423-425; Angew. Chem. Int. Ed. Engl. 1993, 32, 423-425.
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Enders, D.1
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95
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D. Enders, U. Jegelka, B. Dücker, Angew. Chem. 1993, 105, 423-425; Angew. Chem. Int. Ed. Engl. 1993, 32, 423-425.
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96
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0002523004
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Parts of the work on (S)-37 and (R)-37 have been reviewed already: D. Enders, B. Bockstiegel, W. Gatzweiler, U. Jegelka, B. Dücker, L. Wortmann, Chim. Oggi 1997, 15, 20-23.
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97
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D. Enders, C. F. Janeck, J. Runsink, Synlett 2000, 641-643; D. Enders, C. F. Janeck, G. Raabe, Eur. J. Org. Chem. 2000, 3337-3345.
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Enders, D.1
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D. Enders, C. F. Janeck, J. Runsink, Synlett 2000, 641-643; D. Enders, C. F. Janeck, G. Raabe, Eur. J. Org. Chem. 2000, 3337-3345.
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D. Enders, A. Nühring, J. Runsink, G. Raabe, Synthesis 2001, 1406-1414.
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103
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14844330819
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note
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The trisubstituted hydrazones thus obtained can be subjected to a fourth alkylation reaction. These results will be published in due course.
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106
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For the "silyl trick", see: a) D. Enders, J. Adam, D. Klein, T. Otten, Synlett 2000, 1371-1384;
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c) D. Enders, B. B. Lohray, Angew. Chem. 1987, 99, 359-360; Angew. Chem. Int. Ed. Engl. 1987, 26, 351-352.
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14844312406
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note
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Majewski and Nowak (reference [69]) were the first to show the possibility of a double aldol reaction (compare reference [68]). The aldol adduct resulting from dioxanone 33 and benzaldehyde did not need to be protected for the second aldol reaction with cyclohexanecarbaldehyde. However, this was the only example presented, and an 83:9:6:2 mixture of diastereomers was obtained.
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142
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84989509632
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