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9
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(a) Churcher, I.; Beher, D.; Best, J. D.; Castro, J. L.; Clarke, E. E.; Gentry, A.; Harrison, T.; Hitzel, L.; Kay, E.; Kerrad, S.; Lewis, H. D.; Morentin-Gutierrez, P.; Mortishire-Smith, R.; Oakley, P. J.; Reilly, M.; Shaw, D. E.; Shearman, M. S.; Teall, M. R.; Williams, S.; Wrigley, J. D. J. Biorg. Med. Chem. Lett. 2006, 16, 280.
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Mortishire-Smith, R.13
Oakley, P.J.14
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(c) Harrison, T.; Churcher, I.; Beher, D. Curr. Opin. Drug. Disc Dev. 2004, 7, 709.
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Harrison, T.1
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18
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34249809258
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WO 2005080309
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(d) Brands, K. M. J.; Brewer, S.; Davies, A. J.; Dolling, U. H.; Hammond, D. C.; Lieberman, D. R.; Scott, J. P. WO 2005080309.
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Brands, K.M.J.1
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Davies, A.J.3
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Lieberman, D.R.6
Scott, J.P.7
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19
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34249818612
-
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PCT Int. Appl. WO 2004013090
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(e) Brands, K. M. J.; Davies, A. J.; Oakley, P. J.; Scott, J. P.; Shaw, D. E.; Teall, M. R. PCT Int. Appl. WO 2004013090.
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Brands, K.M.J.1
Davies, A.J.2
Oakley, P.J.3
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Teall, M.R.6
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20
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34249828019
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PCT Int. Appl. WO 2003018543
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(f) Churcher, I.; Dinnell, K.; Harrison, T.; Kerrad, S.; Nadin, A. J.; Oakley, P. J.; Shaw, D. E.; Teall, M. R.; Williams, B. J.; Williams, S. PCT Int. Appl. WO 2003018543.
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Churcher, I.1
Dinnell, K.2
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Oakley, P.J.6
Shaw, D.E.7
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Williams, B.J.9
Williams, S.10
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21
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34249799143
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PCT Int. Appl. WO 2002081435
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(g) Castro Pineiro, J. L.; Churcher, I.; Dinnell, K.; Harrison, T.; Kerrad, S.; Nadin, A. J.; Oakley, P. J.; Owens, A. P.; Shaw, D. E.; Teall, M. R.; Williams, B. J.; Williams, S. PCT Int. Appl. WO 2002081435.
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Castro Pineiro, J.L.1
Churcher, I.2
Dinnell, K.3
Harrison, T.4
Kerrad, S.5
Nadin, A.J.6
Oakley, P.J.7
Owens, A.P.8
Shaw, D.E.9
Teall, M.R.10
Williams, B.J.11
Williams, S.12
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22
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34249805551
-
-
Yields reported are of isolated materials corrected for purity as determined by reversed-phase HPLC assay versus authentic standards
-
Yields reported are of isolated materials corrected for purity as determined by reversed-phase HPLC assay versus authentic standards.
-
-
-
-
23
-
-
0024400864
-
-
(a) Blacklock, T. J.; Butcher, J. W.; Sohar, P.; Lamanec, T. R.; Grabowski, E. J. J. J. Org. Chem. 1989, 54, 3907.
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Blacklock, T.J.1
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24
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33947485488
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(b) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140.
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Schultz, H.S.1
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Buc, S.R.3
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25
-
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34249784671
-
-
Sulfone 7 can also be prepared in >90% yield by alkylation of 2,5-difluorobenzylbromide with 4-chlorobenzenesulfinic acid sodium salt in DMF; however, this salt is not commercially available on kilogram scale.
-
Sulfone 7 can also be prepared in >90% yield by alkylation of 2,5-difluorobenzylbromide with 4-chlorobenzenesulfinic acid sodium salt in DMF; however, this salt is not commercially available on kilogram scale.
-
-
-
-
26
-
-
34249827711
-
-
Conditions: (a) LiHMDS
-
2)l;
-
2)l
-
-
-
28
-
-
1842687248
-
-
Scott, J. P.; Hammond, D. C.; Beck, E. M.; Brands, K. M. J.; Davies, A. J.; Dolling, Ulf-H.; Kennedy, D. J. Tetrahedron Lett. 2004, 45, 3345.
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Scott, J.P.1
Hammond, D.C.2
Beck, E.M.3
Brands, K.M.J.4
Davies, A.J.5
Dolling6
Ulf-H7
Kennedy, D.J.8
-
31
-
-
0032482080
-
-
For a recent review of the Mannich reaction: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
-
(c) For a recent review of the Mannich reaction: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
-
-
-
-
32
-
-
34249808047
-
-
Crystallographic data for this compound have been deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via, by emailing data_ request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033, a CCDC 236716
-
Crystallographic data for this compound have been deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif, by emailing data_ request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033. (a) CCDC 236716.
-
-
-
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33
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34249824410
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-
CCDC 236717
-
(b) CCDC 236717.
-
-
-
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34
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46149142610
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(a) Tamura, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
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(1986)
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Tamura, Y.1
Ochiai, H.2
Nakamura, T.3
Yoshida, Z.4
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37
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0000112724
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(c) Jung, M. E.; McCombs, C. A.; Taked, Y.; Pan, Y-G. J. Am. Chem. Soc. 1981, 103, 6677.
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Jung, M.E.1
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Taked, Y.3
Pan, Y.-G.4
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39
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46149142610
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Tamura, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
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(1986)
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Tamura, Y.1
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0141519198
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Zhang, M.; Azhu, L.; Ma, X.; Dai, M.; Lowe, D. Org. Lett. 2003, 5, 1587.
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(2003)
Org. Lett
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Zhang, M.1
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Dai, M.4
Lowe, D.5
-
41
-
-
34249798581
-
-
Hydrogenations with catalysts derived from rhodium or iridium did not indicate any reversal in substrate control, yielding 12 as the major product in each case examined
-
Hydrogenations with catalysts derived from rhodium or iridium did not indicate any reversal in substrate control, yielding 12 as the major product in each case examined.
-
-
-
-
42
-
-
0000676432
-
-
2(cymene) complexes were prepared according to the literature: Mashima, K.; Kusano, K.; Sate, N.; Matsumura, N.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
-
2(cymene) complexes were prepared according to the literature: Mashima, K.; Kusano, K.; Sate, N.; Matsumura, N.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
-
-
-
-
43
-
-
34249784071
-
-
The regiochemistry in the transition states for ruthenium hydride addition to 2 are likely to be identical, but have been assigned arbitrarily pending further mechanistic experimentation.
-
The regiochemistry in the transition states for ruthenium hydride addition to 2 are likely to be identical, but have been assigned arbitrarily pending further mechanistic experimentation.
-
-
-
-
45
-
-
33744813522
-
-
For a detailed study and rationalisation of the conformational bias of aryl, arylsulfonyl geminally substituted tertiary carbon centers, see
-
(a) For a detailed study and rationalisation of the conformational bias of aryl, arylsulfonyl geminally substituted tertiary carbon centers, see: Scott, J. P.; Mullens, P. R.; Brewer, S. E.; Brands, K. J. M.; Chilenski, J. R.; Davies, A. J.; Gibb, A. D.; Lieberman, D. R.; Oliver, S. F.; Dolling, U-H. Org. Biomol. Chem. 2006, 4, 1806.
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(2006)
Org. Biomol. Chem
, vol.4
, pp. 1806
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-
Scott, J.P.1
Mullens, P.R.2
Brewer, S.E.3
Brands, K.J.M.4
Chilenski, J.R.5
Davies, A.J.6
Gibb, A.D.7
Lieberman, D.R.8
Oliver, S.F.9
Dolling, U.-H.10
-
46
-
-
33645781012
-
-
For the application of this conformational bias in an intramolecular nitrile oxide-olefin cycloaddition, see: Scott, J. P, Oliver, S. F, Brands, K. J. M, Brewer, S. E, Daves, A. J, Gibb, A. D, Hands, D, Keen, S. P, Sheen, F. J, Reamer, R. A, Wilson, R. D, Dolling, U. H. J. Org. Chem. 2006, 71, 3086
-
(b) For the application of this conformational bias in an intramolecular nitrile oxide-olefin cycloaddition, see: Scott, J. P.; Oliver, S. F.; Brands, K. J. M.; Brewer, S. E.; Daves, A. J.; Gibb, A. D.; Hands, D.; Keen, S. P.; Sheen, F. J.; Reamer, R. A.; Wilson, R. D.; Dolling, U. H. J. Org. Chem. 2006, 71, 3086.
-
-
-
-
48
-
-
34249812218
-
-
Diastereoselection was determined by reversed-phase HPLC analysis
-
(a) Diastereoselection was determined by reversed-phase HPLC analysis,
-
-
-
-
49
-
-
34249801357
-
-
4 reduction of 4 afforded a 67:33 trans/cis mixture from which the trans isomer could be separated chromatographically.
-
4 reduction of 4 afforded a 67:33 trans/cis mixture from which the trans isomer could be separated chromatographically.
-
-
-
-
50
-
-
34249810777
-
-
13C NMR studies that indicated the presence of two sets of four quaternary carbon signals and isolated AB proton quartets consistent with methylenes adjacent to the nitrile functions.
-
13C NMR studies that indicated the presence of two sets of four quaternary carbon signals and isolated AB proton quartets consistent with methylenes adjacent to the nitrile functions.
-
-
-
-
54
-
-
0002248149
-
-
(d) Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1980, 21, 2671.
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(1980)
Tetrahedron Lett
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, pp. 2671
-
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Broekhof, N.L.J.M.1
Jonkers, F.L.2
van der Gen, A.3
-
55
-
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0018364616
-
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(e) Broekhof, N. L. J. M.; Jonkers, F. L.; van der Gen, A. Tetrahedron Lett. 1979, 20, 2433.
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(1979)
Tetrahedron Lett
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Broekhof, N.L.J.M.1
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57
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0026485005
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(b) Anderson, C. L.; Soderquist, J. A.; Kabalka, G. W. Tetrahedron Lett. 1992, 33, 6915.
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(1992)
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Anderson, C.L.1
Soderquist, J.A.2
Kabalka, G.W.3
-
58
-
-
37049095886
-
-
Incomplete conversion of aldehyde 16, likely due to competing enolization, was observed with methoxymethyldiphenyl phosphine oxide under a variety of conditions: Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Chem. Commun. 1977, 314.
-
Incomplete conversion of aldehyde 16, likely due to competing enolization, was observed with methoxymethyldiphenyl phosphine oxide under a variety of conditions: Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Chem. Commun. 1977, 314.
-
-
-
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