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2
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0035515753
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Nilsson J.W., Thorstensson F., Kvarnström I., Oprea T., Samuelsson B., and Nilsson I. J. Comb. Chem. 3 (2001) 546-553
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Nilsson, J.W.1
Thorstensson, F.2
Kvarnström, I.3
Oprea, T.4
Samuelsson, B.5
Nilsson, I.6
-
5
-
-
67650262074
-
-
For syntheses of nonracemic 2,6-dialkylpiperazines, see
-
For syntheses of nonracemic 2,6-dialkylpiperazines, see:
-
-
-
-
6
-
-
0029947932
-
-
Schanen V., Cherrier M.-P., de Melo S.J., Quirion J.-C., and Husson H.-P. Synthesis (1996) 833-837
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(1996)
Synthesis
, pp. 833-837
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-
Schanen, V.1
Cherrier, M.-P.2
de Melo, S.J.3
Quirion, J.-C.4
Husson, H.-P.5
-
9
-
-
67650246730
-
-
For syntheses of racemic 2,6-dialkylpiperazines, see
-
For syntheses of racemic 2,6-dialkylpiperazines, see:
-
-
-
-
10
-
-
17744400080
-
-
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., and van Maarseveen J.H. Tetrahedron Lett. 46 (2005) 2369-2371
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(2005)
Tetrahedron Lett.
, vol.46
, pp. 2369-2371
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-
Berkheij, M.1
van der Sluis, L.2
Sewing, C.3
den Boer, D.J.4
Terpstra, J.W.5
Hiemstra, H.6
Bakker, W.I.I.7
van den Hoogenband, A.8
van Maarseveen, J.H.9
-
12
-
-
38749153968
-
-
Michael has recently described a concise, highly diastereoselective asymmetric synthesis of trans-2,6-disubstituted piperazines bearing C-2 methyl groups that is complementary to the transformations described in this paper. See:
-
Michael has recently described a concise, highly diastereoselective asymmetric synthesis of trans-2,6-disubstituted piperazines bearing C-2 methyl groups that is complementary to the transformations described in this paper. See:. Cochran B.M., and Michael F.E. Org. Lett. 10 (2008) 329-332
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(2008)
Org. Lett.
, vol.10
, pp. 329-332
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Cochran, B.M.1
Michael, F.E.2
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14
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-
33748274686
-
-
Ferber B., Prestat G., Vogel S., Madec D., and Poli G. Synlett (2006) 2133-2135
-
(2006)
Synlett
, pp. 2133-2135
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-
Ferber, B.1
Prestat, G.2
Vogel, S.3
Madec, D.4
Poli, G.5
-
15
-
-
33644535452
-
-
and references cited therein
-
Viso A., Fernandez de la Pradilla R., Flores A., Garcia A., Tortosa M., and Lopez-Rodriguez M.L. J. Org. Chem. 71 (2006) 1442-1448 and references cited therein
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(2006)
J. Org. Chem.
, vol.71
, pp. 1442-1448
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Viso, A.1
Fernandez de la Pradilla, R.2
Flores, A.3
Garcia, A.4
Tortosa, M.5
Lopez-Rodriguez, M.L.6
-
16
-
-
34548185689
-
-
A portion of these studies have been previously communicated. See:
-
A portion of these studies have been previously communicated. See:. Nakhla J.S., and Wolfe J.P. Org. Lett. 9 (2007) 3279-3282
-
(2007)
Org. Lett.
, vol.9
, pp. 3279-3282
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-
Nakhla, J.S.1
Wolfe, J.P.2
-
17
-
-
67650213537
-
-
For related Pd-catalyzed carboamination reactions between aryl or alkenyl halides and alkenes bearing pendant nitrogen nucleophiles that afford pyrrolidines, isoxazolidines, pyrazolidines, indolines, or imidazoldin-2-ones, see
-
For related Pd-catalyzed carboamination reactions between aryl or alkenyl halides and alkenes bearing pendant nitrogen nucleophiles that afford pyrrolidines, isoxazolidines, pyrazolidines, indolines, or imidazoldin-2-ones, see:
-
-
-
-
24
-
-
64149126749
-
-
For reviews, see:
-
Lemen G.S., Giampietro N.C., Hay M.B., and Wolfe J.P. J. Org. Chem. 74 (2009) 2533-2540 For reviews, see:
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(2009)
J. Org. Chem.
, vol.74
, pp. 2533-2540
-
-
Lemen, G.S.1
Giampietro, N.C.2
Hay, M.B.3
Wolfe, J.P.4
-
27
-
-
67650243417
-
-
For examples of Cu-catalyzed intramolecular carboamination of N-(arylsulfonyl)-2-allylanilines and related derivatives, see
-
For examples of Cu-catalyzed intramolecular carboamination of N-(arylsulfonyl)-2-allylanilines and related derivatives, see:
-
-
-
-
29
-
-
2542624580
-
-
For Pd(II)-catalyzed alkoxycarbonylation of alkenes bearing tethered nitrogen nucleophiles, see:
-
Sherman E.S., Chemler S.R., Tan T.B., and Gerlits O. Org. Lett. 6 (2004) 1573-1575 For Pd(II)-catalyzed alkoxycarbonylation of alkenes bearing tethered nitrogen nucleophiles, see:
-
(2004)
Org. Lett.
, vol.6
, pp. 1573-1575
-
-
Sherman, E.S.1
Chemler, S.R.2
Tan, T.B.3
Gerlits, O.4
-
30
-
-
0000454653
-
-
For carboamination reactions between alkenes and N-allylsulfonamides, see:
-
Harayama H., Abe A., Sakado T., Kimura M., Fugami K., Tanaka S., and Tamaru Y. J. Org. Chem. 62 (1997) 2113-2122 For carboamination reactions between alkenes and N-allylsulfonamides, see:
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2113-2122
-
-
Harayama, H.1
Abe, A.2
Sakado, T.3
Kimura, M.4
Fugami, K.5
Tanaka, S.6
Tamaru, Y.7
-
31
-
-
33746917969
-
-
For carboamination of vinylcyclopropanes, see:
-
Scarborough C.C., and Stahl S.S. Org. Lett. 8 (2006) 3251-3254 For carboamination of vinylcyclopropanes, see:
-
(2006)
Org. Lett.
, vol.8
, pp. 3251-3254
-
-
Scarborough, C.C.1
Stahl, S.S.2
-
32
-
-
84942731093
-
-
For 1,1-carboamination of alkenes, see:
-
Larock R.C., and Yum E.K. Synlett (1990) 529-530 For 1,1-carboamination of alkenes, see:
-
(1990)
Synlett
, pp. 529-530
-
-
Larock, R.C.1
Yum, E.K.2
-
36
-
-
0032501446
-
-
Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459-12467
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(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12459-12467
-
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Ma, D.1
Zhang, Y.2
Yao, J.3
Wu, S.4
Tao, F.5
-
37
-
-
15944369282
-
-
Use of biphasic conditions led to significant erosion of enantiomeric purity. See:
-
Use of biphasic conditions led to significant erosion of enantiomeric purity. See:. Lu Z., and Twieg R.J. Tetrahedron Lett. 46 (2005) 2997-3001
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 2997-3001
-
-
Lu, Z.1
Twieg, R.J.2
-
38
-
-
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:
-
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., and Goodman M. Org. Lett. 1 (1999) 91-94
-
(1999)
Org. Lett.
, vol.1
, pp. 91-94
-
-
Li, H.1
Jiang, X.2
Ye, Y.-H.3
Fan, C.4
Romoff, T.5
Goodman, M.6
-
39
-
-
24144441333
-
-
de Meijere A., and Diederich F. (Eds), Wiley-VCH, Weinheim, Germany
-
Jiang L., and Buchwald S.L. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim, Germany 699-760
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions. 2nd ed.
, pp. 699-760
-
-
Jiang, L.1
Buchwald, S.L.2
-
42
-
-
67650258915
-
-
note
-
In order to achieve complete consumption of starting materials, a ratio of four ligands/Pd atom was employed, as 2:1 ligand/Pd ratios led to only 85-90% conversion.
-
-
-
-
43
-
-
67650231271
-
-
note
-
1-pivaloyl protected substrates afforded only trace amounts of products.
-
-
-
-
44
-
-
67650237809
-
-
note
-
Initial studies on carboaminations of amides such as 5a-c suggest these transformations may be feasible, but further optimization is required; low yields (ca. 10-20%) of the desired products were obtained.
-
-
-
-
45
-
-
67650225679
-
-
For one-pot syntheses of N-aryl indolines or N-aryl pyrrolidines from primary amines or anilines bearing pendant alkenes, see
-
For one-pot syntheses of N-aryl indolines or N-aryl pyrrolidines from primary amines or anilines bearing pendant alkenes, see:
-
-
-
-
46
-
-
67650219179
-
-
Ref. 9b;
-
Ref. 9b;
-
-
-
-
50
-
-
67650225906
-
-
For additional discussion of syn- versus anti-aminopalladation of alkenes, see
-
For additional discussion of syn- versus anti-aminopalladation of alkenes, see:
-
-
-
-
53
-
-
67650219180
-
-
Alkene insertion into late M-H bonds is usually much faster than alkene insertion into late M-C bonds. See
-
Alkene insertion into late M-H bonds is usually much faster than alkene insertion into late M-C bonds. See:
-
-
-
-
56
-
-
67650249899
-
-
The insertion of alkenes into Pd-C bonds in intramolecular Heck reactions occurs through a conformation in which the alkene π-bond and the Pd-C bond are eclipsed. Other possible transition states in which the orientation of the alkene is perpendicular to the M-C bond are significantly higher in energy See
-
The insertion of alkenes into Pd-C bonds in intramolecular Heck reactions occurs through a conformation in which the alkene π-bond and the Pd-C bond are eclipsed. Other possible transition states in which the orientation of the alkene is perpendicular to the M-C bond are significantly higher in energy See:
-
-
-
-
57
-
-
0001232903
-
-
Overman L.E., Abelman M.M., Kucera D.J., Tran V.D., and Ricca D.J. Pure. Appl. Chem. 64 (1992) 1813-1819
-
(1992)
Pure. Appl. Chem.
, vol.64
, pp. 1813-1819
-
-
Overman, L.E.1
Abelman, M.M.2
Kucera, D.J.3
Tran, V.D.4
Ricca, D.J.5
-
59
-
-
2342460950
-
-
The X-ray crystal structure of a known Pd(Ar)(NArR′) complex supports the illustrated trigonal planar geometry of the sp2-hybridized nitrogen atom. See:
-
The X-ray crystal structure of a known Pd(Ar)(NArR′) complex supports the illustrated trigonal planar geometry of the sp2-hybridized nitrogen atom. See:. Yamashita M., and Hartwig J.F. J. Am. Chem. Soc. 126 (2004) 5344-5345
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5344-5345
-
-
Yamashita, M.1
Hartwig, J.F.2
-
60
-
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67650222823
-
-
note
-
Examination of molecular models suggests that low diastereoselectivities would be obtained in reactions that afford cis-2,5-disubstituted pyrrolidines if alkene aminopalladation occurred with the nonbonding nitrogen electrons directed towards the alkene π-system.
-
-
-
-
61
-
-
67650213538
-
-
note
-
An alternative explanation for formation of the cis-2,3-disubstituted piperazine 41 as the major stereoisomer, with low selectivity, would involve cyclization through a chair-like transition state in which the alkene was oriented in a pseudoaxial position (75). However, the alkene pi-system is perpendicular to the Pd-N bond in 75, which is anticipated to lead to high transition state energy. As such, we currently favor the boat-like transition state model for these transformations. For discussion of related transition states in alkene carbopalladation processes, see Ref. 22.{A figure is presented}
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