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Volumn 67, Issue 23, 2002, Pages 8123-8129

Conformationally constrained α-Boc-aminophosphonates via transition metal-catalyzed/curtius rearrangement strategies

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANATION;

EID: 0037111703     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0262208     Document Type: Article
Times cited : (47)

References (95)
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    • (d) See also ref 1a.
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    • note
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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.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2491-2493
    • Schuman, M.1    Trevitt, M.2    Redd, A.3    Gouverneur, V.4
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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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    • 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.
    • (2000) Synlett , pp. 1031-1033
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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.
    • (2001) Synthesis , pp. 612-620
    • Sprott, K.T.1    McReynolds, M.D.2    Hanson, P.R.3
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    • See also refs 15d and 15e
    • 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 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.
    • (1954) Synth. Commun. , vol.14 , pp. 155-161
    • Callant, P.1    D'Haenens, L.2    Vandewalle, M.3
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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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1455-1458
    • Hanson, P.R.1    Sprott, K.T.2    Wrobleski, A.D.3
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    • note
    • 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.
  • 76
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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.
    • (1975) Angew. Chem. , vol.87 , pp. 259-268
    • Regitz, M.1
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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.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3563-3565
    • Roers, R.1    Verdine, G.L.2
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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.
    • (2000) Tetrahedron , vol.56 , pp. 5479-5492
    • Nemes, C.1    Jeannin, L.2    Sapi, J.3    Laronze, M.4    Seghir, H.5    Auge, F.6    Laronze, J.-Y.7
  • 85
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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.
    • (2000) Eur. J. Org. Chem. , pp. 1-15
    • Abele, S.1    Seebach, D.2
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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.
    • (1999) Eur. J. Org. Chem. , pp. 3105-3115
    • 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
  • 88
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    • note
    • The tert-butyldialkylphosphonoacetates are readily prepared using standard Arbuzov reaction of trimethyl phosphite or triallyl phosphite and tert-butyl iodoacetate.
  • 89
    • 2242494969 scopus 로고    scopus 로고
    • note
    • We also attempted the Curtius rearrangement directly from the acid using DPPA; however, the isocyanate peak was never detected by IR.
  • 93
    • 2242442208 scopus 로고    scopus 로고
    • note
    • 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).
  • 94
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    • note
    • Prepared from 1a in our previously reported sequential (2,3)-sigmatropic ylide rearrangement/RCM strategy, see ref 18b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.