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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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Tetrahedron
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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Tetrahedron Lett.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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Synlett
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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For additional uses of RCM in the production of new phosphorus-containing compounds see: (a) Leconte, M.; Jourdan, I.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857-858. (b) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1998, 39, 3939-3942. (c) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119-2123. (d) Hanson, P. R.; Stoianova, D. S. Tetrahedron Lett. 1999, 40, 3297-3300. (e) Trevitt, M.; Gouverneur, V. Tetrahedron Lett. 1999, 40, 7333-7336. (f) Hetherington, L.; Greedy, B.; Gouverneur, V. Tetrahedron 2000, 56, 2053-2060. (g) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772. (h) Schuman, M.; Trevitt, M.; Redd, A.; Gouverneur, V. Angew. Chem., Int. Ed. 2000, 39, 2491-2493. (i) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2000, 41, 8635-8638. (j) Srensen, A. M.; Nielsen, P. Org. Lett. 2000, 2, 4217-4219. (k) Sprott, K. T.; Hanson, P. R. J. Org. Chem 2000, 65, 7913-7918. (l) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031-1033. (m) Sprott, K. T.; McReynolds, M. D.; Hanson, P. R. Synthesis 2001, 612-620. (n) See also refs 15d and 15e.
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73
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84949383846
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For the use of α-diazophosphonates in ICP reactions, see: (a) Callant, P.; D'Haenens, L.; Vandewalle, M. Synth. Commun. 1954, 14, 155-161. (b) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett. 1999, 40, 1455-1458. (c) For a review containing examples of intermolecular cyclopropanation reactions of α-diazophosphonates, see: (d) Regitz, M. Angew. Chem. 1975, 87, 259-268.
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For the use of α-diazophosphonates in ICP reactions, see: (a) Callant, P.; D'Haenens, L.; Vandewalle, M. Synth. Commun. 1954, 14, 155-161. (b) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett. 1999, 40, 1455-1458. (c) For a review containing examples of intermolecular cyclopropanation reactions of α-diazophosphonates, see: (d) Regitz, M. Angew. Chem. 1975, 87, 259-268.
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note
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For the use of α-diazophosphonates in ICP reactions, see: (a) Callant, P.; D'Haenens, L.; Vandewalle, M. Synth. Commun. 1954, 14, 155-161. (b) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett. 1999, 40, 1455-1458. (c) For a review containing examples of intermolecular cyclopropanation reactions of α-diazophosphonates, see: (d) Regitz, M. Angew. Chem. 1975, 87, 259-268.
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For the use of α-diazophosphonates in ICP reactions, see: (a) Callant, P.; D'Haenens, L.; Vandewalle, M. Synth. Commun. 1954, 14, 155-161. (b) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett. 1999, 40, 1455-1458. (c) For a review containing examples of intermolecular cyclopropanation reactions of α-diazophosphonates, see: (d) Regitz, M. Angew. Chem. 1975, 87, 259-268.
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83
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0035926301
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For recent references utilizing the Curtius rearrangement in the synthesis of α-amino acids see: (a) Roers, R.; Verdine, G. L. Tetrahedron Lett. 2001, 42, 3563-3565. (b) Nemes, C.; Jeannin, L.; Sapi, J.; Laronze, M.; Seghir, H.; Auge, F.; Laronze, J.-Y. Tetrahedron 2000, 56, 5479-5492. (c) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15. (d) De Meijere, A.; Ernst, K.; Zuck, B.; Brandl, M.; Kozhushkov, S. I.; Tamm, M.; Yufit, D. S.; Howard, J. A. K.; Labahn, T. Eur. J. Org. Chem. 1999, 3105-3115.
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Tetrahedron Lett.
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, pp. 3563-3565
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Roers, R.1
Verdine, G.L.2
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84
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0034698148
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For recent references utilizing the Curtius rearrangement in the synthesis of α-amino acids see: (a) Roers, R.; Verdine, G. L. Tetrahedron Lett. 2001, 42, 3563-3565. (b) Nemes, C.; Jeannin, L.; Sapi, J.; Laronze, M.; Seghir, H.; Auge, F.; Laronze, J.-Y. Tetrahedron 2000, 56, 5479-5492. (c) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15. (d) De Meijere, A.; Ernst, K.; Zuck, B.; Brandl, M.; Kozhushkov, S. I.; Tamm, M.; Yufit, D. S.; Howard, J. A. K.; Labahn, T. Eur. J. Org. Chem. 1999, 3105-3115.
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(2000)
Tetrahedron
, vol.56
, pp. 5479-5492
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Nemes, C.1
Jeannin, L.2
Sapi, J.3
Laronze, M.4
Seghir, H.5
Auge, F.6
Laronze, J.-Y.7
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85
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0033986387
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For recent references utilizing the Curtius rearrangement in the synthesis of α-amino acids see: (a) Roers, R.; Verdine, G. L. Tetrahedron Lett. 2001, 42, 3563-3565. (b) Nemes, C.; Jeannin, L.; Sapi, J.; Laronze, M.; Seghir, H.; Auge, F.; Laronze, J.-Y. Tetrahedron 2000, 56, 5479-5492. (c) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15. (d) De Meijere, A.; Ernst, K.; Zuck, B.; Brandl, M.; Kozhushkov, S. I.; Tamm, M.; Yufit, D. S.; Howard, J. A. K.; Labahn, T. Eur. J. Org. Chem. 1999, 3105-3115.
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(2000)
Eur. J. Org. Chem.
, pp. 1-15
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Abele, S.1
Seebach, D.2
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86
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0032726768
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For recent references utilizing the Curtius rearrangement in the synthesis of α-amino acids see: (a) Roers, R.; Verdine, G. L. Tetrahedron Lett. 2001, 42, 3563-3565. (b) Nemes, C.; Jeannin, L.; Sapi, J.; Laronze, M.; Seghir, H.; Auge, F.; Laronze, J.-Y. Tetrahedron 2000, 56, 5479-5492. (c) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1-15. (d) De Meijere, A.; Ernst, K.; Zuck, B.; Brandl, M.; Kozhushkov, S. I.; Tamm, M.; Yufit, D. S.; Howard, J. A. K.; Labahn, T. Eur. J. Org. Chem. 1999, 3105-3115.
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(1999)
Eur. J. Org. Chem.
, pp. 3105-3115
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De Meijere, A.1
Ernst, K.2
Zuck, B.3
Brandl, M.4
Kozhushkov, S.I.5
Tamm, M.6
Yufit, D.S.7
Howard, J.A.K.8
Labahn, T.9
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87
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Moore, J. D.; Sprott, K. T.; Wrobleski, A. D.; Hanson, P. R. Org. Lett. 2002, 4, 2357-2360.
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Org. Lett.
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Moore, J.D.1
Sprott, K.T.2
Wrobleski, A.D.3
Hanson, P.R.4
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88
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2242494078
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note
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The tert-butyldialkylphosphonoacetates are readily prepared using standard Arbuzov reaction of trimethyl phosphite or triallyl phosphite and tert-butyl iodoacetate.
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89
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2242494969
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note
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We also attempted the Curtius rearrangement directly from the acid using DPPA; however, the isocyanate peak was never detected by IR.
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91
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0001855961
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(a) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
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J. Am. Chem. Soc.
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Schwab, P.1
Grubbs, R.H.2
Ziller, J.W.3
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92
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33746236970
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(b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
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Angew. Chem., Int. Ed. Engl.
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Schwab, P.1
France, M.B.2
Ziller, J.W.3
Grubbs, R.H.4
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93
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2242442208
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note
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It is interesting to note that conditions incorporated in the Curtius sequence caused complete epimerization at the α-center when starting from a 13:1 mixture of diastereomers (Scheme 1).
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94
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2242439462
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note
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Prepared from 1a in our previously reported sequential (2,3)-sigmatropic ylide rearrangement/RCM strategy, see ref 18b.
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95
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0003241343
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Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
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Organometallics
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Grubbs, R.H.1
Rosen, R.K.2
Timmers, F.J.3
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