-
1
-
-
33845281449
-
-
C-O to C-N catalyzed by Pd(0): (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
-
C-O to C-N catalyzed by Pd(0): (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
-
-
-
-
3
-
-
0002611436
-
-
(c) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1988, 29, 99.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 99
-
-
Hayashi, T.1
Yamamoto, A.2
Ito, Y.3
-
4
-
-
0000533225
-
-
(d) Bystrom, S. E.; Aslanian, R.; Backvall, J.-E. Tetrahedron Lett. 1985, 26, 1749.
-
(1985)
Tetrahedron Lett
, vol.26
, pp. 1749
-
-
Bystrom, S.E.1
Aslanian, R.2
Backvall, J.-E.3
-
5
-
-
0025232768
-
-
(e) Hayashi, T.; Kishi, K.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1990, 31, 1743.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 1743
-
-
Hayashi, T.1
Kishi, K.2
Yamamoto, A.3
Ito, Y.4
-
6
-
-
0033591863
-
-
(f) Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 6761
-
-
Evans, P.A.1
Robinson, J.E.2
Nelson, J.D.3
-
8
-
-
34250897237
-
-
Olefin aminohydroxylation: (h) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 2004; p 309. Mannich:
-
Olefin aminohydroxylation: (h) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 2004; p 309. Mannich:
-
-
-
-
10
-
-
3242668608
-
-
(j) Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 8777
-
-
Matsunaga, S.1
Yoshida, T.2
Morimoto, H.3
Kumagai, N.4
Shibasaki, M.5
-
11
-
-
33846198424
-
-
(k) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F. J. Am. Chem. Soc. 2007, 129, 288.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 288
-
-
Ramasastry, S.S.V.1
Zhang, H.2
Tanaka, F.3
Barbas, C.F.4
-
12
-
-
13444287979
-
-
Streamlining syntheses via late stage C-H oxidation see: a
-
Streamlining syntheses via late stage C-H oxidation see: (a) Fraunhoffer, K. J.; Bachovchin, D. A.; White, M. C. Org. Lett. 2005, 7, 223.
-
(2005)
Org. Lett
, vol.7
, pp. 223
-
-
Fraunhoffer, K.J.1
Bachovchin, D.A.2
White, M.C.3
-
13
-
-
33845745902
-
-
(b) Covell, D. J.; Vermeulen, N. A.; Labenz, N. A.; White, M. C. Angew. Chem., Int. Ed. 2006, 45, 8217.
-
(2006)
Angew. Chem., Int. Ed
, vol.45
, pp. 8217
-
-
Covell, D.J.1
Vermeulen, N.A.2
Labenz, N.A.3
White, M.C.4
-
15
-
-
12344263136
-
-
Elegant examples of late stage C-H hydroxylation and amination see: d
-
Elegant examples of late stage C-H hydroxylation and amination see: (d) Wender, P. A.; Hilinski, M. K.; Mayweg, A. V. W. Org. Lett. 2005, 7, 79.
-
(2005)
Org. Lett
, vol.7
, pp. 79
-
-
Wender, P.A.1
Hilinski, M.K.2
Mayweg, A.V.W.3
-
17
-
-
0035793265
-
-
C-H amination via metal nitrenes: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
-
C-H amination via metal nitrenes: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
-
-
-
-
18
-
-
33646438818
-
-
(b) Kim, M.; Mulcahy, J. V.; Espino, C. G.; Du Bois, J. Org. Lett. 2006, 8, 1073.
-
(2006)
Org. Lett
, vol.8
, pp. 1073
-
-
Kim, M.1
Mulcahy, J.V.2
Espino, C.G.3
Du Bois, J.4
-
19
-
-
26844569944
-
-
(c) Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 14198
-
-
Lebel, H.1
Huard, K.2
Lectard, S.3
-
20
-
-
34250887994
-
-
For single examples of catalytic allylic C-H amination: (a) ref 3b.
-
For single examples of catalytic allylic C-H amination: (a) ref 3b.
-
-
-
-
21
-
-
0001338814
-
-
(b) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
-
(1996)
J. Org. Chem
, vol.61
, pp. 3584
-
-
Larock, R.C.1
Hightower, T.R.2
Hasvold, L.A.3
Peterson, K.P.4
-
22
-
-
0001537435
-
-
(a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674.
-
(1976)
J. Am. Chem. Soc
, vol.98
, pp. 2674
-
-
Hegedus, L.S.1
Allen, G.F.2
Waterman, E.L.3
-
23
-
-
0028832448
-
-
(b) Ronn, M.; Backvall, J. E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749.
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 7749
-
-
Ronn, M.1
Backvall, J.E.2
Andersson, P.G.3
-
24
-
-
34250817336
-
-
ref. 4b
-
(c) ref. 4b.
-
-
-
-
26
-
-
14844317635
-
-
(e) Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 2868
-
-
Brice, J.L.1
Harang, J.E.2
Timokhin, V.I.3
Anastasi, N.R.4
Stahl, S.S.5
-
27
-
-
19744375923
-
-
(a) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 7690
-
-
Alexanian, E.J.1
Lee, C.2
Sorensen, E.J.3
-
29
-
-
9144225503
-
-
Manzoni, M. R.; Zabawa, T. P.; Kasi, D.; Chemler, S. R. Organometallics 2004, 23, 5618.
-
(2004)
Organometallics
, vol.23
, pp. 5618
-
-
Manzoni, M.R.1
Zabawa, T.P.2
Kasi, D.3
Chemler, S.R.4
-
31
-
-
27144440348
-
-
(b) Streuff, J.; Hovelmann, C. H.; Nieger, M.; Muniz, K. J. Am. Chem. Soc. 2005, 127, 14586.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 14586
-
-
Streuff, J.1
Hovelmann, C.H.2
Nieger, M.3
Muniz, K.4
-
32
-
-
23844527400
-
-
(c) 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
-
33
-
-
33845555800
-
-
(a) Akermark, B.; Akermark, G.; Hegedus, L. S.; Zetterberg, K. J. Am. Chem. Soc. 1981, 103, 3037.
-
(1981)
J. Am. Chem. Soc
, vol.103
, pp. 3037
-
-
Akermark, B.1
Akermark, G.2
Hegedus, L.S.3
Zetterberg, K.4
-
34
-
-
0001115723
-
-
and references therein
-
(b) Trost, B. M. Tetrahedron 1977, 33, 2615 and references therein.
-
(1977)
Tetrahedron
, vol.33
, pp. 2615
-
-
Trost, B.M.1
-
35
-
-
18744372130
-
-
(a) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 6970
-
-
Chen, M.S.1
Prabagaran, N.2
Labenz, N.A.3
White, M.C.4
-
36
-
-
33746094649
-
-
(b) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 9032
-
-
Fraunhoffer, K.J.1
Prabagaran, N.2
Sirois, L.E.3
White, M.C.4
-
39
-
-
34250846915
-
-
2O) of EtOC(O)NHTs = 3.7. Taylor, L. D.; Pluhar, M.; Rubin, L. E. J. Polym. Sci., Part B: Polym. Phys. 1967, 5, 77.
-
2O) of EtOC(O)NHTs = 3.7. Taylor, L. D.; Pluhar, M.; Rubin, L. E. J. Polym. Sci., Part B: Polym. Phys. 1967, 5, 77.
-
-
-
-
40
-
-
34250848952
-
-
2. Only ca. 1% of the allylic acetate product observed (Supporting Information, SI-23).
-
2. Only ca. 1% of the allylic acetate product observed (Supporting Information, SI-23).
-
-
-
-
41
-
-
34250866066
-
-
3, and -OC(O)NH(p-OMe)Ph with less acidic N-H bonds showed poor reactivities. Addition of 10 mol% Hunig's base to p-anisyl carbamate substrate gave no significant improvement (SI-9 and ref 24).
-
3, and -OC(O)NH(p-OMe)Ph with less acidic N-H bonds showed poor reactivities. Addition of 10 mol% Hunig's base to p-anisyl carbamate substrate gave no significant improvement (SI-9 and ref 24).
-
-
-
-
42
-
-
34250818569
-
-
1,1-disubstituted and 1,2-disubstituted olefin substrates proceeded with poor conversions (30%) and yields (ca. 8-12% as mixtures of oxidative amination products), (b) Methyl 2-(tosylcarbamoyloxy)pent-4-enoate gave a complex mixture of products (ca. 30% anti-oxazolidinone identified) (SI-8,9).
-
(a) 1,1-disubstituted and 1,2-disubstituted olefin substrates proceeded with poor conversions (30%) and yields (ca. 8-12% as mixtures of oxidative amination products), (b) Methyl 2-(tosylcarbamoyloxy)pent-4-enoate gave a complex mixture of products (ca. 30% anti-oxazolidinone identified) (SI-8,9).
-
-
-
-
43
-
-
33846938595
-
-
Ross, J. E.; Fritsche, T. R.; Sader, H. S.; Jones, R. N. Int. J. Antimicrob. Agents 2007, 29, 295.
-
(2007)
Int. J. Antimicrob. Agents
, vol.29
, pp. 295
-
-
Ross, J.E.1
Fritsche, T.R.2
Sader, H.S.3
Jones, R.N.4
-
44
-
-
0029995939
-
-
Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B. J. Am. Chem. Soc. 1996, 118, 3584.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 3584
-
-
Nagamitsu, T.1
Sunazuka, T.2
Tanaka, H.3
Omura, S.4
Sprengeler, P.A.5
Smith, A.B.6
-
45
-
-
0037124555
-
-
For alternative syntheses see
-
For alternative syntheses see: Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981.
-
(2002)
Tetrahedron
, vol.58
, pp. 4981
-
-
Bonini, C.1
Righi, G.2
-
46
-
-
0037039966
-
-
Lei, A.; Liu, G.; Lu, X. J. Org. Chem. 2002, 67, 974.
-
(2002)
J. Org. Chem
, vol.67
, pp. 974
-
-
Lei, A.1
Liu, G.2
Lu, X.3
-
48
-
-
34250878867
-
-
Unlike allylic C-H oxidation, Pd/sulfoxide-catalyzed allylic C-H amination does not require quinone for functionalization and therefore does not proceed via a serial ligand catalysis mechanism. See ref 10a
-
Unlike allylic C-H oxidation, Pd/sulfoxide-catalyzed allylic C-H amination does not require quinone for functionalization and therefore does not proceed via a serial ligand catalysis mechanism. See ref 10a.
-
-
-
-
50
-
-
34250869414
-
-
1H NMR monitoring at 5, 24, 48, and 72 h (signal/noise > 500:1) (SI-24). The possibility that trace levels of 17 and/or 18 form under standard reaction conditions and contribute to formation of 3a cannot be rigorously excluded.
-
1H NMR monitoring at 5, 24, 48, and 72 h (signal/noise > 500:1) (SI-24). The possibility that trace levels of 17 and/or 18 form under standard reaction conditions and contribute to formation of 3a cannot be rigorously excluded.
-
-
-
-
51
-
-
34250796095
-
-
Previous work (ref 1a and ref 1b) in Pd(0)-mediated allylic substitution reactions has shown that the poor nucleophilic properties of carbamates require the use of their respective anions to achieve reactivity with π-allylpalladium intermediates.
-
Previous work (ref 1a and ref 1b) in Pd(0)-mediated allylic substitution reactions has shown that the poor nucleophilic properties of carbamates require the use of their respective anions to achieve reactivity with π-allylpalladium intermediates.
-
-
-
-
53
-
-
33845938814
-
-
For an alternative-approach to this see
-
For an alternative-approach to this see: Lafrance, M.; Fagnou, K. J. Am. Chem. Soc 2006, 128, 16496.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 16496
-
-
Lafrance, M.1
Fagnou, K.2
|