-
1
-
-
0025368066
-
-
From host-guest complexation of rac -bicyclo[2.2.2]oct-7-ene-2,5-dione and (S)-(-)-10,10-dihydroxy-9,9-biphenanthryl, see
-
From host-guest complexation of rac -bicyclo[2.2.2]oct-7-ene-2,5-dione and (S)-(-)-10,10-dihydroxy-9,9-biphenanthryl, see: Kinoshita, T; Haga, K; Ikai, K; Takeuchi, K. Tetrahedron Lett. 1990, 31, 4057-4060
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Kinoshita, T.1
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2
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0001267980
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Analytical data for racemic 1, see
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Analytical data for racemic 1, see: Ikai, K; Takeuchi, K.; Kinoshita, T; Haga, K.; Komatsu, K; Okamoto, K. J. Org. Chem. 1991, 56, 1052-1058
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84856186682
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Safety Assessment of Diels-Alder Reactions with Highly Reactive Reagents. Org. Process Res. Dev, 2012. Manuscript in preparation
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Abele, S.; Stoessel, F. Safety Assessment of Diels-Alder Reactions with Highly Reactive Reagents. Org. Process Res. Dev, 2012. Manuscript in preparation.
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8
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6444231736
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For bod* ligands, see
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For bod* ligands, see: Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584-13585
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84856186685
-
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Patent application filed, 20 October 2010. Preparation of bicyclo[2.2.2]octane-2-one compounds
-
Abele, S.; Funel, J.-A. Patent application filed, 20 October 2010. Preparation of bicyclo[2.2.2]octane-2-one compounds.
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Abele, S.1
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12
-
-
39049134318
-
-
Reported for the precursor lacking the ketal moiety, see
-
Reported for the precursor lacking the ketal moiety, see: La Bella, A.; Popolla, I.; Felici, M.; Leonelli, F.; Ceccacci, F.; Filocamo, L.; Migneco, L. M.; Bettolo, R. M. ARKIVOC 2008, iii, 80-90
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-
13
-
-
58649123793
-
-
Published after the first 100 g batches of 1 had been produced by our present method according to Scheme 9
-
Published after the first 100 g batches of 1 had been produced by our present method according to Scheme 9: Bella, M.; Schietroma, D. M. S.; Cusella, P. P.; Gasperi, T. Chem. Commun. 2009, 597-599
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Xu, Y.; Ohori, K.; Ohshima, T.; Shibasaki, M. Tetrahedron 2002, 58, 2585-2588
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15
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84856173480
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Enantioselective Michael addition of 2-phenylcyanoacetate to vinyl ketones, see
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Enantioselective Michael addition of 2-phenylcyanoacetate to vinyl ketones, see: Jautze, S.; Peters, R. Angew. Chem., Int. Ed. 2008, 47, 1-6
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8644275468
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19
-
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0029074907
-
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Obtained by β-elimination of benzenesulfenic acid from the intermediate α-phenylsulfoxide, see
-
Obtained by β-elimination of benzenesulfenic acid from the intermediate α-phenylsulfoxide, see: Resek, J. E.; Meyers, A. I. Tetrahedron Lett. 1995, 36, 7051-7054
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0032367786
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33746640446
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0035922367
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24
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33750591030
-
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Cyclohexenone as Michael acceptor, see
-
Cyclohexenone as Michael acceptor, see: Widegren, M.; Dietz, M.; Friberg, A.; Frejd, T.; Hahn-Hägerdahl, B.; Gorwa-Grauslund, M. F.; Katz, M. Synthesis 2006, 3527-3530
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Widegren, M.1
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Hahn-Hägerdahl, B.5
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Katz, M.7
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26
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84856161804
-
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PCT Int. Appl. WO/1998/09942, Due to the toxicity of tin organyls, this is not appropriate for larger scales
-
Martinelli, M.; Moher, E. D. PCT Int. Appl. WO/1998/09942, 1998. Due to the toxicity of tin organyls, this is not appropriate for larger scales.
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(1998)
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Martinelli, M.1
Moher, E.D.2
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28
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0037283351
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Ripin, D. H. B.; Abele, S.; Cai, W.; Blumenkopf, T.; Casavant, J. M.; Doty, J. L.; Flanagan, M.; Koecher, C.; Laue, K. W.; McCarthy, K.; Meltz, C.; Munchhoff, M.; Pouwer, K.; Shah, B.; Sun, J.; Teixeira, J.; Vries, T.; Whipple, D. A.; Wilcox, G. Org. Process Res. Dev. 2003, 7, 115-120
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Ripin, D.H.B.1
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29
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Phosphoric acid, 100 °C, chromatography, 35%, see
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Phosphoric acid, 100 °C, chromatography, 35%, see: Mori, K.; Nakahara, Y.; Matsui, M. Tetrahedron 1972, 28, 3217-3226
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Mori, K.1
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30
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-
0032444128
-
-
Racemate: 2 N HCl, THF, reflux, 24 h, chromatography, 61% rac - 19a, see
-
Racemate: 2 N HCl, THF, reflux, 24 h, chromatography, 61% rac-19a, see: De Santis, B.; Iamiceli, A. L.; Bettolo, R. M.; Migneco, L. M.; Scarpelli, R.; Cercichelli, G.; Fabrizi, G.; Lamba, D. Helv. Chim. Acta 1998, 81, 2375-2387
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31
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0041689590
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Discussion of the endo-exo equilibrium of 19a and 19b, see
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Discussion of the endo-exo equilibrium of 19a and 19b, see: Di Stefano, S.; Leonello, F.; Garofalo, B.; Mandolini, L.; Bettolo, R. M.; Migneco, L. M. Org. Lett. 2002, 4, 2783-2785
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0038356814
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Racemate: phosphoric acid, THF, reflux, 4 h, chromatography, 49% rac - 19a, see
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Racemate: phosphoric acid, THF, reflux, 4 h, chromatography, 49% rac-19a, see: Schmoldt, P.; Mattay, J. Synthesis 2003, 1071-1078
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Schmoldt, P.1
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33646116045
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Chirally pure compound: phosphoric acid, THF, reflux, 4 h, chromatography, 38% 19a, see
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Chirally pure compound: phosphoric acid, THF, reflux, 4 h, chromatography, 38% 19a, see: Tzvetkov, N.; Schmoldt, P.; Neumann, B.; Stammler, H.-G.; Mattay, J. Tetrahedron: Asymmetry 2006, 17, 993-998
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33947093954
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Residual toluene (9% w/w) stemming from malonate 23 was distilled off. (b) Krapcho decarboxylation in DMSO, see
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Delhaye, L.1
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58149162950
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Busacca, C. A.; Cerreta, M.; Dong, Y.; Eriksson, M. C.; Farina, V.; Feng, X.; Kim, J.-Y.; Lorenz, J. C.; Sarvestani, M.; Simpson, R.; Varsolona, R.; Vitous, J.; Campbell, S. J.; Davis, M. S.; Jones, P.-J.; Norwood, D.; Qiu, F.; Beaulieu, P. L.; Duceppe, J.-S.; Haché, B.; Brong, J.; Chiu, F.-T.; Curtis, T.; Kelley, J.; Lo, Y. S.; Powner, T. H. Org. Process Res. Dev. 2008, 12, 603-613
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84856161811
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Chemetall brochure, Organolithium compounds, (accessed Feb 17, 2011)
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Chemetall brochure, Organolithium compounds, http://www.chemetalllithium. com/fileadmin/files-chemetall/Downloads/DL-Organolithium.pdf (accessed Feb 17, 2011).
-
-
-
-
50
-
-
84856166622
-
-
The relative volume of the filter cake was 1.2 vol
-
The relative volume of the filter cake was 1.2 vol.
-
-
-
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33845282179
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Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562
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Anelli, P.L.1
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54
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84856166625
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-
Reference 23a
-
Reference 23a.
-
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55
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0003173772
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Kelly, R. B.; Harley, M. L.; Alward, S. J.; Rej, R. N.; Gowda, G.; Mukhopadhyay, A.; Manchand, P. S. Can. J. Chem. 1983, 61, 269-275
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56
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84856166621
-
-
rac-9a
-
rac-9a.
-
-
-
-
57
-
-
84856186687
-
-
rac - 9b, and
-
rac-9b, and
-
-
-
-
58
-
-
84856186686
-
-
rac-9c
-
rac-9c.
-
-
-
-
61
-
-
84891317706
-
-
This reaction was termed an intramolecular reactive crystallization as well; see: John Wiley & Sons, Inc. Hoboken, NJ
-
This reaction was termed an intramolecular reactive crystallization as well; see: Tung, H.-H.; Paul, E. L.; Midler, P. M.; McCauley, J. A. Crystallization of Organic Compounds: An Industrial Perspective; John Wiley & Sons, Inc.: Hoboken, NJ, 2009.
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(2009)
Crystallization of Organic Compounds: An Industrial Perspective
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Tung, H.-H.1
Paul, E.L.2
Midler, P.M.3
McCauley, J.A.4
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62
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84856161815
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Reference 21
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Reference 21.
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63
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0036214428
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Coons, S.; Javanmard, S.; Collard, D. M.; Kuhar, M. J.; Schweri, M. M.; Deutsch, H. M. Med. Chem. Res. 2002, 11, 24-39
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(2002)
Med. Chem. Res.
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Coons, S.1
Javanmard, S.2
Collard, D.M.3
Kuhar, M.J.4
Schweri, M.M.5
Deutsch, H.M.6
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65
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0000331564
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Methyl- N -(triethylammoniumsulfonyl)carbamate, see
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Methyl- N -(triethylammoniumsulfonyl)carbamate, see: Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744-4745
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(1968)
J. Am. Chem. Soc.
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, pp. 4744-4745
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Atkins, G.M.1
Burgess, E.M.2
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66
-
-
6744245863
-
-
A hyperconjugative interaction was postulated between the n(C - O), the (C1)-(C2), and the forming empty p orital, see
-
A hyperconjugative interaction was postulated between the n(C - O), the (C1)-(C2), and the forming empty p orital, see: Carrupt, P.-A.; Vogel, P. Helv. Chim. Acta 1989, 72, 1008-1028
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(1989)
Helv. Chim. Acta
, vol.72
, pp. 1008-1028
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Carrupt, P.-A.1
Vogel, P.2
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67
-
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0042850891
-
-
Skeletal rearrangements of bicyclo[2.2.2]octyl cation, see
-
Skeletal rearrangements of bicyclo[2.2.2]octyl cation, see: Walborsky, H. M.; Baum, M. E.; Youssef, A. A. J. Am. Chem. Soc. 1961, 83, 988-993
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(1961)
J. Am. Chem. Soc.
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Walborsky, H.M.1
Baum, M.E.2
Youssef, A.A.3
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68
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84856161814
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Reference 1a
-
Reference 1a.
-
-
-
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69
-
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0344643132
-
-
Alternatively, chiral bicyclo[2.2.2]octane-2,5-dione, an intermediate of Takeuchi's synthesis was obtained in 0.45% yield by chromatographic separation of tartrate-derived monoketals of bicyclo[2.2.2]oct-7-ene-2,5-dione, see
-
Alternatively, chiral bicyclo[2.2.2]octane-2,5-dione, an intermediate of Takeuchi's synthesis was obtained in 0.45% yield by chromatographic separation of tartrate-derived monoketals of bicyclo[2.2.2]oct-7-ene-2,5-dione, see: Hill, R. K.; Morton, G. H.; Peterson, J. R.; Walsh, J. A.; Paquette, L. A. J. Org. Chem. 1985, 50, 5528-5533
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(1985)
J. Org. Chem.
, vol.50
, pp. 5528-5533
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Hill, R.K.1
Morton, G.H.2
Peterson, J.R.3
Walsh, J.A.4
Paquette, L.A.5
-
70
-
-
17044390818
-
-
The chiral intermediate bicyclo[2.2.2]octane-2,5-dione (2.3% yield) was obtained by fractional crystallization of the (R)-5-(1-phenylethyl) semioxamazide, see
-
The chiral intermediate bicyclo[2.2.2]octane-2,5-dione (2.3% yield) was obtained by fractional crystallization of the (R)-5-(1-phenylethyl) semioxamazide, see: Otomura, Y.; Okamoto, K.; Hayashi, T. J. Org. Chem. 2005, 70, 2503-2508
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(2005)
J. Org. Chem.
, vol.70
, pp. 2503-2508
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Otomura, Y.1
Okamoto, K.2
Hayashi, T.3
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