-
1
-
-
0035515753
-
-
Nilsson, J. W.; Thorstensson, F.; Kvarnström, I.; Oprea, T.; Samuelsson, B.; Nilsson, I. J. Comb. Chem. 2001, 3, 546.
-
(2001)
J. Comb. Chem
, vol.3
, pp. 546
-
-
Nilsson, J.W.1
Thorstensson, F.2
Kvarnström, I.3
Oprea, T.4
Samuelsson, B.5
Nilsson, I.6
-
2
-
-
19444378658
-
-
For examples of biologically active 2,6-disubstituted piperazines, see: (a) Zheng, G, Dwoskin, L. P, Deaciuc, A. G, Zhu, J, Jones, M. D, Crooks, P. A. Bioorg. Med. Chem. 2005, 13, 3899
-
For examples of biologically active 2,6-disubstituted piperazines, see: (a) Zheng, G.; Dwoskin, L. P.; Deaciuc, A. G.; Zhu, J.; Jones, M. D.; Crooks, P. A. Bioorg. Med. Chem. 2005, 13, 3899.
-
-
-
-
3
-
-
0037122756
-
-
(b) Chu-Moyer, M. Y.; Ballinger, W. E.; Beebe, D. A.; Berger, R.; Coutcher. J. B.: Day, W. W.; Li, J.; Mylari, B. L.; Oates, P. J.; Weekly, R. M. J. Med. Chem. 2002, 45, 511.
-
(2002)
J. Med. Chem
, vol.45
, pp. 511
-
-
Chu-Moyer, M.Y.1
Ballinger, W.E.2
Beebe, D.A.3
Berger, R.4
Coutcher, J.B.5
Day, W.W.6
Li, J.7
Mylari, B.L.8
Oates, P.J.9
Weekly, R.M.10
-
4
-
-
0037366605
-
-
(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
-
(2003)
Chem. Rev
, vol.103
, pp. 893
-
-
Horton, D.A.1
Bourne, G.T.2
Smythe, M.L.3
-
7
-
-
0029947932
-
-
For syntheses of nonracemic 2,6-dialkylpiperazines, see: a
-
For syntheses of nonracemic 2,6-dialkylpiperazines, see: (a) Schanen, V.; Cherrier, M.-P.; de Melo, S. J.; Quirion, J.-C.; Husson, H.-P. Synthesis 1996, 833.
-
(1996)
Synthesis
, pp. 833
-
-
Schanen, V.1
Cherrier, M.-P.2
de Melo, S.J.3
Quirion, J.-C.4
Husson, H.-P.5
-
10
-
-
17744400080
-
-
For syntheses of racemic 2,6-dialkylpiperazines, see: (a) Berkheij, M.; van der Sluis, L.; Sewing, C.; den Boer, D. J.; Terpstra, J. W.; Hiemstra, H.; Bakker, W. I. I.: van den Hoogenband, A.; van Maarseveen, J. H. Tetrahedron Lett. 2005, 46, 2369.
-
For syntheses of racemic 2,6-dialkylpiperazines, see: (a) Berkheij, M.; van der Sluis, L.; Sewing, C.; den Boer, D. J.; Terpstra, J. W.; Hiemstra, H.; Bakker, W. I. I.: van den Hoogenband, A.; van Maarseveen, J. H. Tetrahedron Lett. 2005, 46, 2369.
-
-
-
-
11
-
-
0027506921
-
-
(b) Mouhtaram, M.; Jung, L.; Stambach, J. F. Tetrahedron 1993, 49, 1391.
-
(1993)
Tetrahedron
, vol.49
, pp. 1391
-
-
Mouhtaram, M.1
Jung, L.2
Stambach, J.F.3
-
12
-
-
0042766849
-
-
For selected recent approaches to the synthesis of substituted piperazine derivatives, see: a
-
For selected recent approaches to the synthesis of substituted piperazine derivatives, see: (a) Mercer, G. J.; Sigman, M. S. Org. Lett. 2003, 5, 1591.
-
(2003)
Org. Lett
, vol.5
, pp. 1591
-
-
Mercer, G.J.1
Sigman, M.S.2
-
13
-
-
33748274686
-
-
(b) Ferber. B.; Prestat, G.; Vogel, S.; Madec, D.; Poli, G. Synlett 2006, 2133.
-
(2006)
Synlett
, pp. 2133
-
-
Ferber, B.1
Prestat, G.2
Vogel, S.3
Madec, D.4
Poli, G.5
-
14
-
-
33644535452
-
-
and references cited therein
-
(c) Viso, A.; Fernandez de la Pradilla, R.; Flores, A.; Garcia, A.; Tortosa, M.; Lopez-Rodriguez, M. L. J. Org. Chem. 2006, 71, 1442 and references cited therein.
-
(2006)
J. Org. Chem
, vol.71
, pp. 1442
-
-
Viso, A.1
Fernandez de la Pradilla, R.2
Flores, A.3
Garcia, A.4
Tortosa, M.5
Lopez-Rodriguez, M.L.6
-
19
-
-
27544506294
-
-
(e) Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575.
-
(2005)
Org. Lett
, vol.7
, pp. 2575
-
-
Yang, Q.1
Ney, J.E.2
Wolfe, J.P.3
-
20
-
-
27544515010
-
-
(f) Ney, J. E.; Hay, M. B.; Yang, Q.; Wolfe, J. P. Adv. Synth. Catal. 2005, 347, 1614.
-
(2005)
Adv. Synth. Catal
, vol.347
, pp. 1614
-
-
Ney, J.E.1
Hay, M.B.2
Yang, Q.3
Wolfe, J.P.4
-
23
-
-
33847074190
-
-
(i) Bertand, M. B.; Leathen, M. L.; Wolfe, J. P. Org. Lett. 2007, 9, 457.
-
(2007)
Org. Lett
, vol.9
, pp. 457
-
-
Bertand, M.B.1
Leathen, M.L.2
Wolfe, J.P.3
-
25
-
-
34247203753
-
-
(k) Peng, J.; Lin, W.; Yuan, S.; Chen, Y. J. Org. Chem. 2007, 72, 3145.
-
(2007)
J. Org. Chem
, vol.72
, pp. 3145
-
-
Peng, J.1
Lin, W.2
Yuan, S.3
Chen, Y.4
-
26
-
-
34248572954
-
-
For examples of Cu-catalyzed intramolecular carboamination, see: (a) Sherman, E. S, Fuller, P. H, Kasi, D, Chemler, S. R. J. Org. Chem. 2007, 72, 3896
-
For examples of Cu-catalyzed intramolecular carboamination, see: (a) Sherman, E. S.; Fuller, P. H.; Kasi, D.; Chemler, S. R. J. Org. Chem. 2007, 72, 3896.
-
-
-
-
27
-
-
2542624580
-
-
6, 1573. For Pd(II)-catalyzed alkoxycarbonylation of alkenes bearing tethered nitrogen nucleophiles
-
(b) Sherman E. S.; Chemler, S. R.; Tan, T. B.; Gerlits, O. Org. Lett. 2004, 6, 1573. For Pd(II)-catalyzed alkoxycarbonylation of alkenes bearing tethered nitrogen nucleophiles,
-
(2004)
Org. Lett
-
-
Sherman, E.S.1
Chemler, S.R.2
Tan, T.B.3
Gerlits, O.4
-
28
-
-
0000454653
-
-
see: c, For carboamination reactions between alkenes and N-allylsulfonamides
-
see: (c) Harayama, H.; Abe, A.; Sakado, T.; Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru Y. J. Org. Chem. 1997, 62, 2113. For carboamination reactions between alkenes and N-allylsulfonamides,
-
(1997)
J. Org. Chem
, vol.62
, pp. 2113
-
-
Harayama, H.1
Abe, A.2
Sakado, T.3
Kimura, M.4
Fugami, K.5
Tanaka, S.6
Tamaru, Y.7
-
29
-
-
33746917969
-
-
see: d, 3251. For carboamination of vinylcyclopropanes, see
-
see: (d) Scarborough, C. C.; Stahl, S. S. Org. Lett. 2006, 8, 3251. For carboamination of vinylcyclopropanes, see:
-
(2006)
Org. Lett
, vol.8
-
-
Scarborough, C.C.1
Stahl, S.S.2
-
30
-
-
84942731093
-
-
529. For 1,1-carboamination of alkenes, see
-
(e) Larock, R. C.; Yum, E. K. Synlett 1990, 529. For 1,1-carboamination of alkenes, see:
-
(1990)
Synlett
-
-
Larock, R.C.1
Yum, E.K.2
-
31
-
-
0028147903
-
-
(f) Larock, R. C.; Yang, H.; Weinreb, S. M.; Herr, R. J. J. Org. Chem. 1994, 59, 4172.
-
(1994)
J. Org. Chem
, vol.59
, pp. 4172
-
-
Larock, R.C.1
Yang, H.2
Weinreb, S.M.3
Herr, R.J.4
-
32
-
-
0032501446
-
-
Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 12459
-
-
Ma, D.1
Zhang, Y.2
Yao, J.3
Wu, S.4
Tao, F.5
-
34
-
-
0033564987
-
-
DEPBT = 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one. Use of other reagents (e.g., DCC/HOBT or CDI) resulted in partial epimerization to afford products with ∼85-90% ee. See: Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91.
-
DEPBT = 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one. Use of other reagents (e.g., DCC/HOBT or CDI) resulted in partial epimerization to afford products with ∼85-90% ee. See: Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1, 91.
-
-
-
-
35
-
-
34548180339
-
-
Cu-catalyzed N-arylation reactions of alanine afforded products with ≤93% ee. See ref 9
-
Cu-catalyzed N-arylation reactions of alanine afforded products with ≤93% ee. See ref 9.
-
-
-
-
37
-
-
0042291889
-
-
Astruc, D, Ed, Wiley, VCH: Weinheim, Germany
-
(b) Hartwig, J. F. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley, VCH: Weinheim, Germany, 2002; p 107.
-
(2002)
Modern Arene Chemistry
, pp. 107
-
-
Hartwig, J.F.1
-
39
-
-
34548181078
-
-
Initial studies on carboaminations of amides such as 4 or 6 suggest these transformations may be feasible, but further optimization is required; low yields ca. 10-20, of the desired products were obtained
-
Initial studies on carboaminations of amides such as 4 or 6 suggest these transformations may be feasible, but further optimization is required; low yields (ca. 10-20%) of the desired products were obtained.
-
-
-
-
40
-
-
34548161389
-
-
Diastereomeric ratios observed in crude reaction mixtures were identical with those obtained upon isolation. In some cases the minor diastereomer could be separated by careful chromatography. See the Supporting Information for complete details
-
Diastereomeric ratios observed in crude reaction mixtures were identical with those obtained upon isolation. In some cases the minor diastereomer could be separated by careful chromatography. See the Supporting Information for complete details.
-
-
-
-
41
-
-
34548186669
-
-
Preliminary efforts to employ a N1 Boc-protected substrate resulted in the formation of a 1:1 mixture of diastereomers. Attempts to cyclize substrates bearing N1 Piv or Ac groups have thus far been unsuccessful.
-
Preliminary efforts to employ a N1 Boc-protected substrate resulted in the formation of a 1:1 mixture of diastereomers. Attempts to cyclize substrates bearing N1 Piv or Ac groups have thus far been unsuccessful.
-
-
-
-
42
-
-
0000857523
-
-
Alkene insertion into late M-H bonds is usually much faster than alkene insertion into late M-C bonds. See: (a) Brookhart, M, Hauptman, E, Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394
-
Alkene insertion into late M-H bonds is usually much faster than alkene insertion into late M-C bonds. See: (a) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394.
-
-
-
-
43
-
-
0001111590
-
-
(b) Siegbahn, P. E. M.; Stromberg, S.; Zetterberg, K. Organometallics 1996, 15, 5542.
-
(1996)
Organometallics
, vol.15
, pp. 5542
-
-
Siegbahn, P.E.M.1
Stromberg, S.2
Zetterberg, K.3
-
44
-
-
34548153257
-
-
The formation of unsaturated five-membered heterocycles analogous to 10 and 11 is generally not observed in N-aryl-2-benzylpyrrolidine-forming reactions. Instead, the generation of regioisomeric N-aryl-2-methyl-3- arylpyrrolidine side products, which result from reversible β-hydride elimination/reinsertion processes, is observed. These side products are usually formed in ca. 10% yield, whereas the combined yields of 10 and 11 is usually ca. 20-30%. For further discussion, see refs 7a and 7j.
-
The formation of unsaturated five-membered heterocycles analogous to 10 and 11 is generally not observed in N-aryl-2-benzylpyrrolidine-forming reactions. Instead, the generation of regioisomeric N-aryl-2-methyl-3- arylpyrrolidine side products, which result from reversible β-hydride elimination/reinsertion processes, is observed. These side products are usually formed in ca. 10% yield, whereas the combined yields of 10 and 11 is usually ca. 20-30%. For further discussion, see refs 7a and 7j.
-
-
-
|