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52949124348
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Jpn. Kokai Tokkyo Koho, Jpn.
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Patent, JP 09048791
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Nishikiori, T.1
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Mizuno, S.5
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33846111293
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1, see: Tsuchiya, S.; Sunazuka, T.; Hirose, T.; Mori, R.; Tanaka, T.; Iwatsuki, M.; Omura, S. Org. Lett. 2006, 8, 5577; and references therein.
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1, see: Tsuchiya, S.; Sunazuka, T.; Hirose, T.; Mori, R.; Tanaka, T.; Iwatsuki, M.; Omura, S. Org. Lett. 2006, 8, 5577; and references therein.
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5
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0033948004
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For other recent approaches to 2-iminoimidazolidines, see: a
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For other recent approaches to 2-iminoimidazolidines, see: (a) Dardonville, C.; Goya, P.; Rozas, I.; Alsasua, A.; Martín, M. I.; Borrego, M. J. Bioorg. Med. Chem. 2000, 8, 1567.
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Goya, P.2
Rozas, I.3
Alsasua, A.4
Martín, M.I.5
Borrego, M.J.6
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0034680580
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(b) Isobe, T.; Fukuda, K.; Yamaguchi, K.; Seki, H.; Tokunaga, T.; Ishikawa, T. J. Org. Chem. 2000, 65, 7779.
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Seki, H.4
Tokunaga, T.5
Ishikawa, T.6
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0035492332
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(c) Matosiuk, D.; Fidecka, S.; Antkiewicz-Michaluk, L.; Dybala, I.; Koziol, A. E. Eur. J. Med. Chem. 2001, 36, 783.
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Eur. J. Med. Chem
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Matosiuk, D.1
Fidecka, S.2
Antkiewicz-Michaluk, L.3
Dybala, I.4
Koziol, A.E.5
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8
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0037424747
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(d) Dennis, M.; Hall, L. M.; Murphy, P. J.; Thornhill, A. J.; Nash, R.; Winters, A. L.; Hursthouse, M. B.; Light, M. E.; Horton, P. Tetrahedron Lett. 2003, 44, 3075.
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(2003)
Tetrahedron Lett
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Dennis, M.1
Hall, L.M.2
Murphy, P.J.3
Thornhill, A.J.4
Nash, R.5
Winters, A.L.6
Hursthouse, M.B.7
Light, M.E.8
Horton, P.9
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9
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8744318421
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(e) AbouJneid, R.; Ghoulami, S.; Martin, M.-T.; Dau, E. T. H.; Travert, N.; Al-Mourabit, A. Org. Lett. 2004, 6, 3933.
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(2004)
Org. Lett
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AbouJneid, R.1
Ghoulami, S.2
Martin, M.-T.3
Dau, E.T.H.4
Travert, N.5
Al-Mourabit, A.6
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10
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2942733486
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(f) Sanière, L.; Leman, L.; Bourguignon, J.-J.; Dauban, P.; Dodd, R. H. Tetrahedron 2004, 60, 5889.
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(2004)
Tetrahedron
, vol.60
, pp. 5889
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Sanière, L.1
Leman, L.2
Bourguignon, J.-J.3
Dauban, P.4
Dodd, R.H.5
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33646438818
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(g) Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073.
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Org. Lett
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Kim, M.1
Mulcahy, J.V.2
Espino, C.G.3
Du Bois, J.4
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12
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24044531286
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For a review, see
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For a review, see: Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188.
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(2005)
Angew. Chem. Int. Ed
, vol.44
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Bräse, S.1
Gil, C.2
Knepper, K.3
Zimmermann, V.4
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14
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33845292599
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See also
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(b) See also: Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523.
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(2007)
Tetrahedron
, vol.63
, pp. 523
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Palacios, F.1
Alonso, C.2
Aparicio, D.3
Rubiales, G.4
de los5
Santos, J.M.6
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15
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0031909221
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and references therein
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Cooper, R. G.; Etheridge, C. J.; Stewart, L.; Marshall, J.; Rudginsky, S.; Cheng, S. H.; Miller, A. D. Chem. Eur. J. 1998, 4, 137; and references therein.
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(1998)
Chem. Eur. J
, vol.4
, pp. 137
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Cooper, R.G.1
Etheridge, C.J.2
Stewart, L.3
Marshall, J.4
Rudginsky, S.5
Cheng, S.H.6
Miller, A.D.7
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16
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0032532253
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Bis(diphenylphosphino)ethane has been used to address similar problems in Staudinger and Mitsunobu reactions, see: O'Neil, I. A.; Thompson, S.; Murray, C. L.; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787.
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Bis(diphenylphosphino)ethane has been used to address similar problems in Staudinger and Mitsunobu reactions, see: O'Neil, I. A.; Thompson, S.; Murray, C. L.; Kalindjian, S. B. Tetrahedron Lett. 1998, 39, 7787.
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17
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52949097164
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2) gave 7 (0.24 g, 71%) as a white solid.
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2) gave 7 (0.24 g, 71%) as a white solid.
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18
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52949094192
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Selected Spectroscopic Data: 7: mp 152-153°C (from CH 2Cl2-Et2O, 1H NMR (400 MHz, CDCl3, δ, 7.81 (d, J, 8.3 Hz, 2 H, ArH, 7.71 (s, 1 H, NH, 7.29-7.37 (m, 5 H, ArH, 7.22 (d, J, 8.3 Hz, 2 H, ArH, 5.25 (s, 2 H, OCH2Ph, 3.90-3.95 (m, 2 H, 3.60-3.65 (m, 2 H, 2.40 (s, 3 H, Me, 13C NMR (100.5 MHz, CDCl3, δ, 154.1 (C, 150.8 (C, 142.6 (C, 139.7 (C, 135.1 (C, 129.3 (CH, 128.6 (CH, 128.3 (CH, 128.0 (CH, 126.3 (CH, 68.5 (CH2, 43.9 (CH2, 39.9 (CH2, 21.5 (Me, IR (neat, 3315, 2919, 1753, 1621 cm-1. MS (FAB, m/z, 374 [M, H, 330. HRMS (FAB , m/z [M, H, calcd for C18H 20N3O4S: 374.1175; found: 374.1179. 16: [α]D24 47 c, 1.2, EtOH, 1H NM
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8S: 776.3693; found: 776.3692.
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19
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52949142151
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This data has been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. Deposition number: CCDC 679310
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This data has been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. Deposition number: CCDC 679310.
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20
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52949097557
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R [(R)-9] = 14.8 min.
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R [(R)-9] = 14.8 min.
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-
-
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21
-
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0031849499
-
-
and references cited therein. For example, see
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For example, see: Hodgkinson, T. J.; Shipman, M. Synthesis 1998, 1141; and references cited therein.
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(1998)
Synthesis
, pp. 1141
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Hodgkinson, T.J.1
Shipman, M.2
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22
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52949091082
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2, 16 h, 90%).
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2, 16 h, 90%).
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-
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23
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52949124349
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This contamination arises from the fact that solid NH4Cl is used to quench the dissolving metal reduction and TFA is used as a co-solvent in the subsequent purification by silica gel chromatography. The effective molarity of 17 in D2O, from which the yield could be estimated, was determined by adding known quantities of 1,4-dioxane to the sample and subsequent quantification of the dioxane/17 ratio by 1H NMR integration
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1H NMR integration.
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