-
3
-
-
0030598062
-
-
Kim, J.-M.; Wilson, T. E.; Norman, T. C.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309-5312.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 5309-5312
-
-
Kim, J.-M.1
Wilson, T.E.2
Norman, T.C.3
Schultz, P.G.4
-
4
-
-
5144223004
-
-
Kazmierski, W. M.; Furfine, E.; Gray-Nunez, Y.; Spaltenstein, A.; Wright, L. Bioorg. Med. Chem. Lett. 2004, 14, 5685-5687.
-
(2004)
Bioorg. Med. Chem. Lett.
, vol.14
, pp. 5685-5687
-
-
Kazmierski, W.M.1
Furfine, E.2
Gray-Nunez, Y.3
Spaltenstein, A.4
Wright, L.5
-
6
-
-
33745548063
-
-
Ley, S. V., Knight, J. G., Eds.; Thieme: Stuttgart
-
Sartori, G.; Maggi, R. in Science of Synthesis (Houben-Weyl Methods of Molecular Transformations); Ley, S. V., Knight, J. G., Eds.; Thieme: Stuttgart, 2005; Vol. 18, pp 665-758.
-
(2005)
Science of Synthesis (Houben-Weyl Methods of Molecular Transformations)
, vol.18
, pp. 665-758
-
-
Sartori, G.1
Maggi, R.2
-
7
-
-
33646438818
-
-
For other recent approaches to the synthesis of cyclic ureas, see: (a) Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073-1076.
-
(2006)
Org. Lett.
, vol.8
, pp. 1073-1076
-
-
Kim, M.1
Mulcahy, J.V.2
Espino, C.G.3
Du Bois, J.4
-
8
-
-
27144440348
-
-
(b) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586-14587.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 14586-14587
-
-
Streuff, J.1
Hövelmann, C.H.2
Nieger, M.3
Muñiz, K.4
-
9
-
-
23844527400
-
-
(c) Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250-11251.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 11250-11251
-
-
Zabawa, T.P.1
Kasi, D.2
Chemler, S.R.3
-
10
-
-
21844470799
-
-
and references therein
-
(d) Kim, M. S.; Kim, Y.-W.; Hahm, H. S.; Jang, J. W.; Lee, W. K.; Ha, H.-J. Chem. Commun. 2005, 3062-3064 and references therein.
-
(2005)
Chem. Commun.
, pp. 3062-3064
-
-
Kim, M.S.1
Kim, Y.-W.2
Hahm, H.S.3
Jang, J.W.4
Lee, W.K.5
Ha, H.-J.6
-
11
-
-
19744362485
-
-
(e) Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308-7309.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 7308-7309
-
-
Bar, G.L.J.1
Lloyd-Jones, G.C.2
Booker-Milburn, K.I.3
-
12
-
-
0032538362
-
-
Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
-
(1998)
Angew. Chem., Int. Ed.
, vol.37
, pp. 2580-2627
-
-
Lucet, D.1
Le Gall, T.2
Mioskowski, C.3
-
13
-
-
4544265647
-
-
(a) Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3605-3608
-
-
Ney, J.E.1
Wolfe, J.P.2
-
15
-
-
1242269280
-
-
For related reactions that provide tetrahydrofuran products, see: (a) Wolfe, J. P.; Rossi, M. A. J. Am. Chem. Soc. 2004, 126, 1620-1621.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 1620-1621
-
-
Wolfe, J.P.1
Rossi, M.A.2
-
17
-
-
0001835856
-
-
For a two-step carboamination strategy involving ureidomercuration followed by radical-mediated alkylation, see: Danishefsky, S.; Taniyama, E.; Webb, R. R., II. Tetrahedron Lett. 1983, 24, 11-14.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 11-14
-
-
Danishefsky, S.1
Taniyama, E.2
Webb II, R.R.3
-
18
-
-
33845280828
-
-
Tamaru has described Pd(II)-catalyzed Wacker-type carbonylation reactions of N-allylureas and O-allylcarbamates that effect ring closure with concomitant C-C bond formation to afford imidazolidin-2-ones and oxazolidin-2-ones bearing carbonyl functionality at C-4. See: (a) Tamaru, Y.; Hojo, M.; Higashimura, H.; Yoshida, Z.-i. J. Am. Chem. Soc. 1988, 110, 3994-4002.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 3994-4002
-
-
Tamaru, Y.1
Hojo, M.2
Higashimura, H.3
Yoshida, Z.-I.4
-
19
-
-
0000454653
-
-
(b) Harayama, H.; Abe, A.; Sakado, T.; Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1997, 62, 2113-2122.
-
(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
-
20
-
-
33745580578
-
-
note
-
Xantphos = 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene; dppe = 1,2-bis(diphenylphosphino)ethane; dppf = 1,1′-bis(diphenylphosphino) ferrocene.
-
-
-
-
21
-
-
33745551291
-
-
note
-
t-Bu in the absence of Pd.
-
-
-
-
22
-
-
33745557387
-
-
note
-
1H NMR analysis.
-
-
-
-
23
-
-
33745531968
-
-
note
-
tBu in the absence of Pd.
-
-
-
-
24
-
-
33745525221
-
-
note
-
Substrates 4-7, 20, 22, 25, and 27 were obtained in 79-97% yield from treatment of the corresponding allylamine with the appropriate isocyanate as described above.
-
-
-
-
25
-
-
1442311143
-
-
(a) Suh, M.-J.; Kim, S. W.; Beak, S. I.; Ha, H.-J.; Lee, W. K. Synlett 2004, 489-492.
-
(2004)
Synlett
, pp. 489-492
-
-
Suh, M.-J.1
Kim, S.W.2
Beak, S.I.3
Ha, H.-J.4
Lee, W.K.5
-
26
-
-
0030029735
-
-
(b) Kise, N.; Kashiwagi, K.; Watanabe, M.; Yoshida, J.-i. J. Org. Chem. 1996, 61, 428-429.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 428-429
-
-
Kise, N.1
Kashiwagi, K.2
Watanabe, M.3
Yoshida, J.-I.4
-
27
-
-
19944429372
-
-
(c) Santos, A. G.; Pereira, J.; Afonso, C. A. M.; Frenking, G. Chem.-Eur. J. 2005, 11, 330-343.
-
(2005)
Chem.-Eur. J.
, vol.11
, pp. 330-343
-
-
Santos, A.G.1
Pereira, J.2
Afonso, C.A.M.3
Frenking, G.4
-
28
-
-
27544506294
-
-
Attempts to transform substrates bearing unprotected N3 moieties led to the formation of products resulting from tandem N-arylation and carboamination in low yield (ca. 30%). For a related reaction of aliphatic amines, see: Yang, Q.; Ney, J. E.; Wolfe, J. P. Org. Lett. 2005, 7, 2575-2578.
-
(2005)
Org. Lett.
, vol.7
, pp. 2575-2578
-
-
Yang, Q.1
Ney, J.E.2
Wolfe, J.P.3
-
29
-
-
33745532362
-
-
note
-
1H NMR COSY and nOe experiments. See the Supporting Information for complete details of stereochemical assignments.
-
-
-
-
30
-
-
20944448962
-
-
2Me-catalyzed carboaminations of N-(p-methoxyphenyl)-2-(cyclopent-2-enylethyl)amine. See: Ney, J. E.; Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 8644-8651.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 8644-8651
-
-
Ney, J.E.1
Wolfe, J.P.2
-
31
-
-
33745569321
-
-
note
-
A small amount of N-(cyclohex-2-enyl)aniline was observed as a side product in this reaction.
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