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1
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77956943226
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Zaminer, J.; Brockmann, C.; Huy, P.; Opitz, R.; Reuter, C.; Beyermann, M.; Freund, C.; Müller, M.; Oschkinat, H.; Kühne, R.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2010, 49, 7111-7115
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Müller, M.8
Oschkinat, H.9
Kühne, R.10
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Tong, Y.; Fobian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. Bioorg. Med. Chem. Lett. 1998, 8, 1679-l682
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Tong, Y.1
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36649013845
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Einsiedel, J.1
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78651504804
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Tong, Y.; Fobian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. Bioorg. Med. Chem. Lett. 2008, 18, 1931-1938
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6
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9844223916
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Jackson, D. Y.; Quan, C.; Artis, D. R.; Rawson, T.; Blackburn, B.; Struble, M.; Fitzgerald, G.; Chan, K.; Mullins, S.; Burnier, J. P.; Fairbrother, W. J.; Clark, K.; Berisini, M.; Chui, H.; Renz, M.; Jones, S.; Fong, S. J. Med. Chem. 1997, 40, 3359-3368
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Fitzgerald, G.7
Chan, K.8
Mullins, S.9
Burnier, J.P.10
Fairbrother, W.J.11
Clark, K.12
Berisini, M.13
Chui, H.14
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7
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0028224169
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Hereides, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry 1994, 5, 351-354
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Tetrahedron: Asymmetry
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Hereides, C.1
Hubmann, H.P.2
Lotter, H.3
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8
-
-
78651513989
-
-
Latest example
-
Latest example: DeSolms, S. J.
-
-
-
Desolms, S.J.1
-
9
-
-
78651511971
-
-
U.S. Patent 5,872,135, 1999; CAN 130:196955
-
U.S. Patent 5,872,135, 1999; CAN 130:196955.
-
-
-
-
10
-
-
0025231348
-
-
Further examples: ref 3b-c
-
Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270-275. Further examples: ref 3b-c
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(1990)
J. Org. Chem.
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, pp. 270-275
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Chung, J.Y.L.1
Wasicak, J.T.2
Arnold, W.A.3
May, C.S.4
Nadzan, A.M.5
Holladay, M.W.6
-
11
-
-
78651495257
-
-
Recent variants of this method exploit an organocatalytic key step
-
Recent variants of this method exploit an organocatalytic key step
-
-
-
-
12
-
-
35748967901
-
-
Rios, H. R.; Ibrahem, I.; Vesely, J.; Sundén, H.; Córdova, A. Tetrahedron Lett. 2007, 48, 8695-8699
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(2007)
Tetrahedron Lett.
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, pp. 8695-8699
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Rios, H.R.1
Ibrahem, I.2
Vesely, J.3
Sundén, H.4
Córdova, A.5
-
14
-
-
78651511418
-
-
For other syntheses of compounds of type 2, see
-
For other syntheses of compounds of type 2, see
-
-
-
-
15
-
-
3543014960
-
-
Soloshonok, V. A.; Ueki, H.; Tiwari, R.; Cai, C.; Hruby, V. J. J. Org. Chem. 2004, 69, 4984-4990
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Soloshonok, V.A.1
Ueki, H.2
Tiwari, R.3
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Hruby, V.J.5
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16
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33751500400
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Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875-2874
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(1991)
J. Org. Chem.
, vol.56
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Kanemasa, S.1
Tatsukawa, A.2
Wada, E.3
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17
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-
0033040773
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Damour, D.; Pulicani, J.-P.; Vuilhorgne, M.; Mignani, S. Synlett 1999, 786-788
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(1999)
Synlett
, pp. 786-788
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Damour, D.1
Pulicani, J.-P.2
Vuilhorgne, M.3
Mignani, S.4
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18
-
-
16244401304
-
-
Ball, L.; Kühne, R.; Schneider-Mergner, J.; Oschkinat, H. Angew. Chem. Int. Ed. 2005, 44, 2852-2869
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(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 2852-2869
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Ball, L.1
Kühne, R.2
Schneider-Mergner, J.3
Oschkinat, H.4
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19
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-
49049108952
-
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Freund, C.; Schmalz, H.-G.; Sticht, J.; Kühne, R. Handb. Exp. Pharmacol. 2008, 186, 407-429
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(2008)
Handb. Exp. Pharmacol.
, vol.186
, pp. 407-429
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Freund, C.1
Schmalz, H.-G.2
Sticht, J.3
Kühne, R.4
-
20
-
-
78651497505
-
-
For noncatalytic 1,4-additions to substituted dehydroprolines, see
-
For noncatalytic 1,4-additions to substituted dehydroprolines, see
-
-
-
-
21
-
-
0030248652
-
-
Ezquerra, J.; Escribano, A.; Rubio, A.; Remuififin, M. J.; Vaquero, J. J. Tetrahedron: Asymmetry 1996, 7, 2613-2626
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(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2613-2626
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Ezquerra, J.1
Escribano, A.2
Rubio, A.3
Remuififin, M.J.4
Vaquero, J.J.5
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22
-
-
0037238331
-
-
Toyooka, N.; Okumura, M.; Himiyama, T.; Nakazawa, A.; Nemoto, H. Synlett 2003, 55-58
-
(2003)
Synlett
, pp. 55-58
-
-
Toyooka, N.1
Okumura, M.2
Himiyama, T.3
Nakazawa, A.4
Nemoto, H.5
-
23
-
-
78651512633
-
-
Reviews
-
Reviews
-
-
-
-
24
-
-
0000597854
-
-
In, Vol. 4;, Eds.; Pergamon: Oxford,; pp
-
Schmalz, H.-G. In Comprehensive Organic Synthesis, Vol. 4; Trost, M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; pp 199 -236.
-
(1991)
Comprehensive Organic Synthesis
, pp. 199-236
-
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Schmalz, H.-G.1
Trost, M.2
Fleming, I.3
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26
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-
51049122142
-
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Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pamies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796-2823
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(2008)
Chem. Rev.
, vol.108
, pp. 2796-2823
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Alexakis, A.1
Bäckvall, J.E.2
Krause, N.3
Pamies, O.4
Diéguez, M.5
-
27
-
-
34147221694
-
-
For a recent contribution from this laboratory, see:; Angew. Chem., Int. Ed. 2008, 47, 7718-7721
-
Lopez, F.; Minnaard, A. J.; Feringa, B. L. Acc. Chem. Res. 2007, 40, 179-188 For a recent contribution from this laboratory, see: Robert, T.; Velder, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2008, 47, 7718-7721
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(2007)
Acc. Chem. Res.
, vol.40
, pp. 179-188
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Lopez, F.1
Minnaard, A.J.2
Feringa, B.L.3
Robert, T.4
Velder, J.5
Schmalz, H.-G.6
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28
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33748619096
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Webb, R. G.; Haskell, M. W.; Stammer, C. H. J. Org. Chem. 1969, 34, 576-580
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(1969)
J. Org. Chem.
, vol.34
, pp. 576-580
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Webb, R.G.1
Haskell, M.W.2
Stammer, C.H.3
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32
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0025061893
-
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Shin, C.; Takahashi, N.; Yonezawa, Y. Chem. Pharm. Bull. 1990, 38, 2020-2023
-
(1990)
Chem. Pharm. Bull.
, vol.38
, pp. 2020-2023
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Shin, C.1
Takahashi, N.2
Yonezawa, Y.3
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33
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0024316562
-
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Purvis, M. B.; LeFevre, J. W.; Jones, V. L.; Kingston, D. G. I.; Biot, A. M.; Gossolé, F. J. Am. Chem. Soc. 1989, 111, 5931-5935
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(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 5931-5935
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Purvis, M.B.1
Lefevre, J.W.2
Jones, V.L.3
Kingston, D.G.I.4
Biot, A.M.5
Gossolé, F.6
-
34
-
-
78651512365
-
-
For the NCS-oxidation of amines to N -chloroamines, see
-
For the NCS-oxidation of amines to N -chloroamines, see
-
-
-
-
35
-
-
0031584878
-
-
Furneaux, R. H.; Limberg, G.; Tyler, P. C.; Schramm, V. L. Tetrahedron 1997, 53, 2915-2930
-
(1997)
Tetrahedron
, vol.53
, pp. 2915-2930
-
-
Furneaux, R.H.1
Limberg, G.2
Tyler, P.C.3
Schramm, V.L.4
-
37
-
-
78651482993
-
-
3 nor pyridine could be replaced by each other. Pyridine proved not to be basic enough to induce HCl elimination (7 to 8) while we assume pyridine to act as a catalyst in the acylation of 8
-
3 nor pyridine could be replaced by each other. Pyridine proved not to be basic enough to induce HCl elimination (7 to 8) while we assume pyridine to act as a catalyst in the acylation of 8.
-
-
-
-
38
-
-
78651488051
-
-
With 1.5 equiv of Cbz-Cl/pyridine the yield of 3a dropped to 30%
-
With 1.5 equiv of Cbz-Cl/pyridine the yield of 3a dropped to 30%.
-
-
-
-
40
-
-
84985273200
-
-
Quinkert, G.; Schmalz, H.-G.; Walzer, E.; Gross, S.; Kowaczyk-Przewloka, T.; Schierloh, C.; Dürner, G.; Bats, J. W.; Kessler, H. Liebigs. Ann. Chem. 1988, 283-315
-
(1988)
Liebigs. Ann. Chem.
, pp. 283-315
-
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Quinkert, G.1
Schmalz, H.-G.2
Walzer, E.3
Gross, S.4
Kowaczyk-Przewloka, T.5
Schierloh, C.6
Dürner, G.7
Bats, J.W.8
Kessler, H.9
-
41
-
-
78651483274
-
-
1H NMR of the purified sample
-
1H NMR of the purified sample.
-
-
-
-
42
-
-
0027151899
-
-
Boger, D. L.; Yohannes, D.; Zhou, J.; Patane, M. A. J. Am. Chem. Soc. 1993, 115, 3420-3430
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3420-3430
-
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Boger, D.L.1
Yohannes, D.2
Zhou, J.3
Patane, M.A.4
-
43
-
-
0000106921
-
-
Not unexpected, the diastereomers could not be separated by column chromatography; see ref 6 and
-
Not unexpected, the diastereomers could not be separated by column chromatography; see ref 6 and Sarges, R.; Tretter, J. R. J. Org. Chem. 1974, 39, 1710-1716
-
(1974)
J. Org. Chem.
, vol.39
, pp. 1710-1716
-
-
Sarges, R.1
Tretter, J.R.2
-
44
-
-
78651479309
-
-
1H NMR (400 MHz). The nonconverted starting material (rac-10) was re-isolated as a mixture of trans and cis diastereomers
-
1H NMR (400 MHz). The nonconverted starting material (rac-10) was re-isolated as a mixture of trans and cis diastereomers.
-
-
-
-
46
-
-
78651500902
-
-
For reviews, see
-
For reviews, see
-
-
-
-
48
-
-
0038468227
-
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Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875
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(1996)
Chem. Rev.
, vol.96
, pp. 835-875
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Ager, D.J.1
Prakash, I.2
Schaad, D.R.3
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0010629372
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Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichimica Acta 1997, 30, 1-24
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(1997)
Aldrichimica Acta
, vol.30
, pp. 1-24
-
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Ager, D.J.1
Prakash, I.2
Schaad, D.R.3
-
50
-
-
78651518256
-
-
Gacs-Baitz, E.; Delle Monache, G.; Misiti, D.; Nevolam, L.; Botta, B.; Zappia, G.; Cancelliere, G. Curr. Org. Synth. 2007, 4, 238-307
-
(2007)
Curr. Org. Synth.
, vol.4
, pp. 238-307
-
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Gacs-Baitz, E.1
Delle Monache, G.2
Misiti, D.3
Nevolam, L.4
Botta, B.5
Zappia, G.6
Cancelliere, G.7
-
51
-
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78651500124
-
-
1H NMR. The assumed trans-configuration of both major isomers was confirmed after hydrolysis to 2a. The formation of minor amounts of cis -isomers cannot be excluded because of the complexity of the NMR spectra on the stage of 15
-
1H NMR. The assumed trans-configuration of both major isomers was confirmed after hydrolysis to 2a. The formation of minor amounts of cis -isomers cannot be excluded because of the complexity of the NMR spectra on the stage of 15.
-
-
-
-
52
-
-
84985531889
-
-
3-mediated 1,4-addition of a vinyl-Cu reagent to 14 (according to) proceeded in 82% yield, however, with lower selectivity (dr = 3.2:1)
-
3-mediated 1,4-addition of a vinyl-Cu reagent to 14 (according to Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1986, 25, 947-959) proceeded in 82% yield, however, with lower selectivity (dr = 3.2:1)
-
(1986)
Angew. Chem., Int. Ed. Engl.
, vol.25
, pp. 947-959
-
-
Yamamoto, Y.1
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53
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0001597804
-
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Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144
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(1987)
Tetrahedron Lett.
, vol.28
, pp. 6141-6144
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Evans, D.A.1
Britton, T.C.2
Ellman, J.A.3
-
54
-
-
78651506723
-
-
1H NMR (integration of the H-2 signals at ca. 5.5 ppm)
-
1H NMR (integration of the H-2 signals at ca. 5.5 ppm).
-
-
-
-
56
-
-
37049091241
-
-
Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495-496
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(1979)
J. Chem. Soc., Chem. Commun.
, pp. 495-496
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Lott, R.S.1
Chauhan, V.S.2
Stammer, C.H.3
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14444272282
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Dragovich, P. S.; Webber, S. E.; Babine, R. E.; Fuhrman, S. A.; Patick, A. K. J. Med. Chem. 1998, 41, 2813-2818
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(1998)
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Dragovich, P.S.1
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Patick, A.K.5
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