-
1
-
-
0032538362
-
-
For leading reviews, see: a
-
For leading reviews, see: (a) Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
-
(1998)
Angew. Chem., Int. Ed
, vol.37
, pp. 2580
-
-
Lucet, D.1
Gall, T.L.2
Mioskowski, C.3
-
3
-
-
33745110538
-
-
(c) Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug. Des. 2006, 67, 101.
-
(2006)
Chem. Biol. Drug. Des
, vol.67
, pp. 101
-
-
Kotti, S.R.S.S.1
Timmons, C.2
Li, G.3
-
4
-
-
33847087811
-
-
For examples of metal-mediated diaminations, see: Co: (a) Becker, P. N, White, M. A, Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676, Hg
-
For examples of metal-mediated diaminations, see: Co: (a) Becker, P. N.; White, M. A.; Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676, Hg:
-
-
-
-
6
-
-
0001362632
-
-
Os
-
(c) Fristad, W. E.; Brandvold, T. A.; Peterson, J. R.; Thompson, S. R. J. Org. Chem. 1985, 50, 3647. Os:
-
(1985)
J. Org. Chem
, vol.50
, pp. 3647
-
-
Fristad, W.E.1
Brandvold, T.A.2
Peterson, J.R.3
Thompson, S.R.4
-
7
-
-
33847090307
-
-
(d) Chong, A. O.; Oshima, K.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 3420.
-
(1977)
J. Am. Chem. Soc
, vol.99
, pp. 3420
-
-
Chong, A.O.1
Oshima, K.2
Sharpless, K.B.3
-
12
-
-
0035915127
-
-
For metal-catalyzed diamination with TsNCh or TsNClNa, see: a
-
For metal-catalyzed diamination with TsNCh or TsNClNa, see: (a) Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed. 2001, 40, 4277.
-
(2001)
Angew. Chem., Int. Ed
, vol.40
, pp. 4277
-
-
Li, G.1
Wei, H.-X.2
Kim, S.H.3
Carducci, M.D.4
-
13
-
-
0037067329
-
-
(b) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777.
-
(2002)
J. Org. Chem
, vol.67
, pp. 4777
-
-
Wei, H.-X.1
Kim, S.H.2
Li, G.3
-
14
-
-
33646896262
-
-
(c) Masuyama, Y.; Ohtsuka, M.; Harima, M.; Kurusu, Y. Heterocycles 2006, 67, 503.
-
(2006)
Heterocycles
, vol.67
, pp. 503
-
-
Masuyama, Y.1
Ohtsuka, M.2
Harima, M.3
Kurusu, Y.4
-
15
-
-
19744362485
-
-
Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc 2005, 127, 7308.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 7308
-
-
Bar, G.L.J.1
Lloyd-Jones, G.C.2
Booker-Milburn, K.I.3
-
16
-
-
23844527400
-
-
(a) Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 11250
-
-
Zabawa, T.P.1
Kasi, D.2
Chemler, S.R.3
-
18
-
-
27144440348
-
-
Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 14586
-
-
Streuff, J.1
Hövelmann, C.H.2
Nieger, M.3
Muñiz, K.4
-
19
-
-
33846624362
-
-
Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 762
-
-
Du, H.1
Zhao, B.2
Shi, Y.3
-
20
-
-
34250863844
-
-
For a related diamination of terminal olefins at allylic and homoallylic carbons via C-H activation, see: Du, H, Yuan, W, Zhao, B, Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496
-
For a related diamination of terminal olefins at allylic and homoallylic carbons via C-H activation, see: Du, H.; Yuan, W.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 7496.
-
-
-
-
21
-
-
34547198807
-
-
Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589.
-
(2007)
Org. Lett
, vol.9
, pp. 2589
-
-
Yuan, W.1
Du, H.2
Zhao, B.3
Shi, Y.4
-
22
-
-
0042401093
-
-
Greene, F. D.; Stowell, J. C.; Bergmark, W. R. J. Org. Chem. 1969, 34, 2254.
-
(1969)
J. Org. Chem
, vol.34
, pp. 2254
-
-
Greene, F.D.1
Stowell, J.C.2
Bergmark, W.R.3
-
23
-
-
0003593740
-
-
For a leading review on diaziridinones, see:, Hassner, A, Ed, John Wiley & Sons, Inc, New York
-
For a leading review on diaziridinones, see: Heine, H. W. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; John Wiley & Sons, Inc.: New York, 1983; p 547.
-
(1983)
The Chemistry of Heterocyclic Compounds
, pp. 547
-
-
Heine, H.W.1
-
24
-
-
0001186123
-
-
Prepared based on reported procedure: Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ozmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
-
Prepared based on reported procedure: Timberlake, J. W.; Alender, J.; Garner, A. W.; Hodges, M. L.; Ozmeral, C.; Szilagyi, S.; Jacobus, J. O. J. Org. Chem. 1981, 46, 2082.
-
-
-
-
25
-
-
84858497844
-
-
3 (0.1 mL) and tri-n-butylphosphine (0.020 mL, 0.08 mmol). After the mixture was stirred at room temperature for 10 min, styrene (5a) (0.042 g, 0.40 mmol) and di-tert-butylthiadiaziridine 1,1-dioxide (6) (0.124 g, 0.60 mmol) were added (for solid olefins, they were added together with CuCl). The reaction mixture was stirred at 50 °C for 24 h and purified by flash chromatography (silica gel, petroleum ether: ethyl acetatexhloroform = 15:1:1.5) to give the diamination product 7a as a white solid (0.080 g, 65%).
-
3 (0.1 mL) and tri-n-butylphosphine (0.020 mL, 0.08 mmol). After the mixture was stirred at room temperature for 10 min, styrene (5a) (0.042 g, 0.40 mmol) and di-tert-butylthiadiaziridine 1,1-dioxide (6) (0.124 g, 0.60 mmol) were added (for solid olefins, they were added together with CuCl). The reaction mixture was stirred at 50 °C for 24 h and purified by flash chromatography (silica gel, petroleum ether: ethyl acetatexhloroform = 15:1:1.5) to give the diamination product 7a as a white solid (0.080 g, 65%).
-
-
-
-
26
-
-
84858497845
-
-
The deprotection with BaCO3·HCl has also been investigated with additional substrates. For example, both the rert-butyl and sulfonyl groups of compound 7h were cleanly removed in 91% yield. Compound 7k was deprotected in 70% yield with a slightly modified procedure small amount of ethanol was added to improve solubility of 7k and the reaction time was extended to 24 h, However, compounds 7l-n decomposed under this deprotection condition. For a reductive deprotection of sulfamide with LiAlH4, see ref 5a
-
4, see ref 5a.
-
-
-
-
27
-
-
0000414557
-
-
For a leading review on metal-promoted radical reactions, see
-
For a leading review on metal-promoted radical reactions, see: Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
-
(1994)
Chem. Rev
, vol.94
, pp. 519
-
-
Iqbal, J.1
Bhatia, B.2
Nayyar, N.K.3
-
28
-
-
0032732016
-
-
For leading reviews on CuX-catalyzed atom transfer reactions see: a
-
For leading reviews on CuX-catalyzed atom transfer reactions see: (a) Patten, T. E.; Matyjaszewski, K. Acc. Chem. Res. 1999, 32, 895.
-
(1999)
Acc. Chem. Res
, vol.32
, pp. 895
-
-
Patten, T.E.1
Matyjaszewski, K.2
-
30
-
-
0001253023
-
-
For leading references on nitrogen-centered radicals, see:, Renaud, P, Sibi, P, Eds, Wiley-VCH: Weinheim, Germany
-
For leading references on nitrogen-centered radicals, see: Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 407.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 407
-
-
Stella, L.1
-
31
-
-
34247130947
-
-
(b) Guin, J.; Mück-Lichtenfeld, C.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2007, 129, 4498.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 4498
-
-
Guin, J.1
Mück-Lichtenfeld, C.2
Grimme, S.3
Studer, A.4
-
32
-
-
0001565380
-
-
For leading references on Cu(I)-catalyzed homolytic cleavage of N-O bonds of oxaziridines, see: (a) Aubé, J.; Peng, X.; Wang, Y.; Takusagawa, F. J. Am. Chem. Soc. 1992, 114, 5466.
-
For leading references on Cu(I)-catalyzed homolytic cleavage of N-O bonds of oxaziridines, see: (a) Aubé, J.; Peng, X.; Wang, Y.; Takusagawa, F. J. Am. Chem. Soc. 1992, 114, 5466.
-
-
-
-
34
-
-
0032490962
-
-
(c) Black, D. StC; Edwards, G. L.; Laaman, S. M. Tetrahedron Lett. 1998, 39, 5853.
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 5853
-
-
Black, D.S.1
Edwards, G.L.2
Laaman, S.M.3
-
36
-
-
0000220284
-
-
For a leading review on organocopper reagents, see
-
For a leading review on organocopper reagents, see: Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
-
(1992)
Org. React
, vol.41
, pp. 135
-
-
Lipshutz, B.H.1
Sengupta, S.2
-
37
-
-
0034098001
-
-
For examples, see: a
-
For examples, see: (a) Casapullo, A.; Bifulco, G.; Bruno, I.; Riccio, R. J. Nat. Prod. 2000, 63, 447.
-
(2000)
J. Nat. Prod
, vol.63
, pp. 447
-
-
Casapullo, A.1
Bifulco, G.2
Bruno, I.3
Riccio, R.4
-
38
-
-
0037149689
-
-
(b) Miyake, F. Y.; Yakushijin, K.; Home, D. A. Org. Lett. 2002, 4, 941.
-
(2002)
Org. Lett
, vol.4
, pp. 941
-
-
Miyake, F.Y.1
Yakushijin, K.2
Home, D.A.3
-
39
-
-
20144388985
-
-
(c) Kumar, V.; Guo, D.; Cassel, J. A.; Daubert, J. D.; DeHaven, R. N.; DeHaven-Hudkins, D. L.; Gauntner, E. K.; Gottshall, S. L.; Greiner, S. L.; Koblish, M.; Little, P. J.; Mansson, E.; Maycock, A. L. Bioorg. Med. Chem. Lett. 2005, 15, 1091.
-
(2005)
Bioorg. Med. Chem. Lett
, vol.15
, pp. 1091
-
-
Kumar, V.1
Guo, D.2
Cassel, J.A.3
Daubert, J.D.4
DeHaven, R.N.5
DeHaven-Hudkins, D.L.6
Gauntner, E.K.7
Gottshall, S.L.8
Greiner, S.L.9
Koblish, M.10
Little, P.J.11
Mansson, E.12
Maycock, A.L.13
|