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1
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70350589093
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Recent Advances in the Synthesis of Heterocycles via RCM
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For selected reviews on the synthesis of heterocyclic compounds by using metathesis reactions, see: a, Eds, G. W. Gribble, J. A. Joule, Pergamon Press, Elmsford, NY
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For selected reviews on the synthesis of heterocyclic compounds by using metathesis reactions, see: a) M. A. Walters, "Recent Advances in the Synthesis of Heterocycles via RCM" in Progress in Heterocyclic Chemistry (Eds.: G. W. Gribble, J. A. Joule), Pergamon Press, Elmsford, NY, 2003, vol. 15, p. 1;
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Walters, M.A.1
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for a specific review on the synthesis of nitrogen-containing compounds by using RCM reactions, see: c A. J. Phillips, A. D. Abell, Aldrichim. Acta 1999, 32, 75;
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for a specific review on the synthesis of nitrogen-containing compounds by using RCM reactions, see: c) A. J. Phillips, A. D. Abell, Aldrichim. Acta 1999, 32, 75;
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4
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1342290467
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for a specific review on the synthesis of nitrogen-containing compounds by using CM reactions, see: d A. J. Vernall, A. D. Abell, Aldrichim. Acta 2003, 36, 93;
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for a specific review on the synthesis of nitrogen-containing compounds by using CM reactions, see: d) A. J. Vernall, A. D. Abell, Aldrichim. Acta 2003, 36, 93;
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5
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36549001142
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for an account on the synthesis of polycyclic compounds (including some nitrogen-containing compounds) by using metathesis reaction, see: e
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for an account on the synthesis of polycyclic compounds (including some nitrogen-containing compounds) by using metathesis reaction, see: e) S. Kotha, K. Lahiri, Synlett 2007, 2767;
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for reviews on sequential metathesis reactions in norbornene derivatives, including 2-azabicyclo[2.2.1]hept-5-en-3-one systems, see: g O. Arjona, A. G. Csákÿ, J. Plumet, Eur. J. Org. Chem. 2003, 611;
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for reviews on sequential metathesis reactions in norbornene derivatives, including 2-azabicyclo[2.2.1]hept-5-en-3-one systems, see: g) O. Arjona, A. G. Csákÿ, J. Plumet, Eur. J. Org. Chem. 2003, 611;
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9
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34147121488
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for a recent report on the use of N-Boc-7-azabicyclo[2.2.1]hept-5- ene in the synthesis of pyrrolidine derivatives by the ROM/CM sequence, see: i J. Carreras, A. Avenoza, J. H. Busto, J. M. Peregrina, Org. Lett. 2007, 9, 1235.
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for a recent report on the use of N-Boc-7-azabicyclo[2.2.1]hept-5- ene in the synthesis of pyrrolidine derivatives by the ROM/CM sequence, see: i) J. Carreras, A. Avenoza, J. H. Busto, J. M. Peregrina, Org. Lett. 2007, 9, 1235.
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Sandford, M.S.1
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53849141062
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An alternative procedure by using acryloyl chloride and HNa in THF gave, -19 in 70% yield
-
An alternative procedure by using acryloyl chloride and HNa in THF gave (-)-19 in 70% yield.
-
-
-
-
36
-
-
0034734340
-
-
This precatalyst is specially useful in catalyzing different metathesis reactions in electron-deficient substrates, see: a S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168
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This precatalyst is specially useful in catalyzing different metathesis reactions in electron-deficient substrates, see: a) S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168,
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37
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b) S. Randl, S. Gessler, H. Wakamatsu, S. Blechert, Synlett 2001, 430.
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Randl, S.1
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38
-
-
53849131584
-
-
When precatalyst 26 was used, compound 39 arising from a double CM reaction was also isolated in 6% yield:
-
When precatalyst 26 was used, compound 39 arising from a double CM reaction was also isolated in 6% yield:
-
-
-
-
39
-
-
0038215596
-
-
The role of chelation effects in the course of the CM reactions has been highlighted in the illustrative review of Connon and (Chemical Equation Presented) Blechert, see: a) S. J. Connon, S. Blechert, Angew. Chem. Int. Ed. 2003, 42, 1900, see in particular pp. 1906-1907;
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The role of chelation effects in the course of the CM reactions has been highlighted in the illustrative review of Connon and (Chemical Equation Presented) Blechert, see: a) S. J. Connon, S. Blechert, Angew. Chem. Int. Ed. 2003, 42, 1900, see in particular pp. 1906-1907;
-
-
-
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40
-
-
0344006321
-
-
in relation to this, see also the comments included in: A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012, see in particular pp. 3019-3020.
-
b) in relation to this, see also the comments included in: A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012, see in particular pp. 3019-3020.
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-
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41
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0035794963
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See, for instance
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See, for instance: T. L. Choi, A. G. Chaterjee, R. H. Grubbs, Angew. Chem. Int. Ed. 2001, 40, 1277.
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42
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0343776189
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Chelation effects were probably responsible for some of the unexpected regioselectivities observed in ROM/CM and ROM/CM/RCMsequences in several oxa- and azanorbornene derivatives. See, for instance: a O. Arjona, A. G. Csákÿ, M. C. Murcia, J. Plumet, J. Org. Chem. 1999, 64, 9739;
-
Chelation effects were probably responsible for some of the unexpected regioselectivities observed in ROM/CM and ROM/CM/RCMsequences in several oxa- and azanorbornene derivatives. See, for instance: a) O. Arjona, A. G. Csákÿ, M. C. Murcia, J. Plumet, J. Org. Chem. 1999, 64, 9739;
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44
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0034714323
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The occurrence of the structural motif pyrrolizidin-3-one is widespread in plants and, less extensively, in insects and molds. For a review on the synthetic approaches to these compounds, see: a X. L. M. Despinoy, H. McNab, Tetrahedron 2000, 56, 6359;
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The occurrence of the structural motif pyrrolizidin-3-one is widespread in plants and, less extensively, in insects and molds. For a review on the synthetic approaches to these compounds, see: a) X. L. M. Despinoy, H. McNab, Tetrahedron 2000, 56, 6359;
-
-
-
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45
-
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34249804136
-
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and references cited therein; for two recent references, see: b
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for two recent references, see: b) R. Schobert, A. Wicklein, Synthesis 2007, 1499, and references cited therein;
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Schobert, R.1
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38849084550
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47
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85120239090
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for the synthesis of enantiopure polyhydroxylated pyrrolizidine alkaloids by using RCM reactions, see: d D. Muroni, M. Mucceda, A. Saba, Tetrahedron Lett. 2008, 49, 2373.
-
for the synthesis of enantiopure polyhydroxylated pyrrolizidine alkaloids by using RCM reactions, see: d) D. Muroni, M. Mucceda, A. Saba, Tetrahedron Lett. 2008, 49, 2373.
-
-
-
-
48
-
-
33646865927
-
-
Pyrrolizidine derivatives have been obtained from cyclopentene-yne compounds by means of ROM/CM in the presence of ethylene as the CM reagent and by using first- and second-generation Grubb's Ru precatalyst, see: H. Wakamatsu, Y. Sato, R. Fujita, M. Mori, Heterocycles 2006, 67, 89
-
Pyrrolizidine derivatives have been obtained from cyclopentene-yne compounds by means of ROM/CM in the presence of ethylene as the CM reagent and by using first- and second-generation Grubb's Ru precatalyst, see: H. Wakamatsu, Y. Sato, R. Fujita, M. Mori, Heterocycles 2006, 67, 89.
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