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(c) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
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(e) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734.
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(f) Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079.
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0033615304
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For some recent examples of asymmetric conjugate addition reactions with nitrogen nucleophiles to furnish β-amino ketones see: (a) Myers, J. K, Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959
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For some recent examples of asymmetric conjugate addition reactions with nitrogen nucleophiles to furnish β-amino ketones see: (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
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9
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(c) Sibi, M. P.; Prabagaran, N.; Ghorpade, S. G.; Jasperse, C. P. J. Am. Chem. Soc. 2003, 125, 11796.
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(d) Yamigawa, N.; Qin, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419.
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11
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(e) Chen, Y. K.; Yoshida, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
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(a) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
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Espino, C.G.1
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(b) Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed. 2004, 43, 4349.
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Fiori, K.W.1
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14
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47749112120
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A sulfamate product analogous to 4 was generated via a chemoselective Rh-nitrene-based reaction in 43% yield: (c) Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220.
-
A sulfamate product analogous to 4 was generated via a chemoselective Rh-nitrene-based reaction in 43% yield: (c) Zalatan, D. N.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 9220.
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15
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(d) Milczek, E.; Boudet, N.; Blakey, S. Angew. Chem., Int. Ed. 2008, 47, 6825.
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(e) Liang, J.-L.; Yuan, S.-X.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2002, 41, 3465.
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17
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38349004623
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Interestingly, high chemoselectivities and reactivities have been reported for intermolecular Rh-nitrene allylic aminations of internal olefins: Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
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Interestingly, high chemoselectivities and reactivities have been reported for intermolecular Rh-nitrene allylic aminations of internal olefins: Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
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18
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1042276609
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Linear allylic C-H acetoxylation: (a) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
-
Linear allylic C-H acetoxylation: (a) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346.
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-
-
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19
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18744372130
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Branched allylic C-H esterification: (b) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
-
Branched allylic C-H esterification: (b) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970.
-
-
-
-
20
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33746094649
-
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Oxidative C-H macrolactonization. (c) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
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Oxidative C-H macrolactonization. (c) Fraunhoffer, K. J.; Prabagaran, N.; Sirois, L. E.; White, M. C. J. Am. Chem. Soc. 2006, 128, 9032.
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-
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21
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30444437460
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For a linear allylic acetoxylation reaction using DMA solvent see: d
-
For a linear allylic acetoxylation reaction using DMA solvent see: (d) Mistudome, T.; Umetani, T.; Nosaka, N.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Angew. Chem., Int. Ed. 2006, 45, 481.
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Mistudome, T.1
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Kaneda, K.7
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22
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54849441648
-
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Linear allylic C-H alkylation: (a) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
-
Linear allylic C-H alkylation: (a) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
-
-
-
-
23
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67650292726
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For a system that also uses Pd(II)/bis-sulfoxide catalysis see: Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
-
(b) For a system that also uses Pd(II)/bis-sulfoxide catalysis see: Lin, S.; Song, C.-X.; Cai, G.-X.; Wang, W.-H.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 12901.
-
-
-
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24
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34250877913
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Intramolecular allylic C-H amination to furnish 1,2-amino alcohol motifs: Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
-
Intramolecular allylic C-H amination to furnish 1,2-amino alcohol motifs: Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274.
-
-
-
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25
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41449083866
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Intermolecular allylic C-H amination to furnish linear (E)-allylic amines using N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile: (a) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
-
Intermolecular allylic C-H amination to furnish linear (E)-allylic amines using N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile: (a) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
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-
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27
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69049095824
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In press, doi: /10.1021/ja903939k. For a similar system using DMA solvent see: (c) Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
-
In press, doi: /10.1021/ja903939k. For a similar system using DMA solvent see: (c) Liu, G.; Yin, G.; Wu, L. Angew. Chem., Int. Ed. 2008, 47, 4733.
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28
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13444287979
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(a) Fraunhoffer, K. F.; Bachovchin, D. A.; White, M. C. Org. Lett. 2005, 7, 223.
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(b) Covell, D. J.; Vermeulen, N. A.; Labenz, N. A.; White, M. C. Angew. Chem., Int. Ed. 2006, 45, 8217.
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0035793265
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Carbamate and N-tosyl carbamate substrates have been observed to exclusively form 5-membered ring oxazolidinone products in nitrene-based systems: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
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Carbamate and N-tosyl carbamate substrates have been observed to exclusively form 5-membered ring oxazolidinone products in nitrene-based systems: (a) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
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31
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(b) Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198.
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Lebel, H.1
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32
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69049114888
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The inclusion of catalytic amine base, recently discovered to promote intermolecular allylic C-H aminations with N-tosyl carbamate nucleophiles (ref 8b), gave a minor increase in yield for substrate 2a (15% → 37%); however, the diastereoselectivity was significantly diminished (5.1:1 → 1.8:1 syn:anti).
-
The inclusion of catalytic amine base, recently discovered to promote intermolecular allylic C-H aminations with N-tosyl carbamate nucleophiles (ref 8b), gave a minor increase in yield for substrate 2a (15% → 37%); however, the diastereoselectivity was significantly diminished (5.1:1 → 1.8:1 syn:anti).
-
-
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33
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33845555454
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This effect has explicitly been demonstrated in the oxidative amination of olefins via electrophilic Pd(II) catalysis: (a) Hegedus, L. S, McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444
-
This effect has explicitly been demonstrated in the oxidative amination of olefins via electrophilic Pd(II) catalysis: (a) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
-
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34
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0001338814
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(b) Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
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35
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0028328337
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Pd(0)-mediated allylic substitution of cyclic carbonates to carbamates proceeds via anionic nitrogen nucleophiles: Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
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Pd(0)-mediated allylic substitution of cyclic carbonates to carbamates proceeds via anionic nitrogen nucleophiles: Bando, T.; Harayama, H.; Fukazawa, Y.; Shiro, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1994, 59, 1465.
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84962408511
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Relative pKa values were based upon benzoic acid analogues: (a) Tao, L.; Han, J.; Tao, F-.M. J. Phys. Chem. A 2008, 112, 775.
-
Relative pKa values were based upon benzoic acid analogues: (a) Tao, L.; Han, J.; Tao, F-.M. J. Phys. Chem. A 2008, 112, 775.
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37
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(b) Maran, F.; Celadon, D.; Severin, M. G.; Vianello, E. J. Am. Chem. Soc. 1991, 113, 9320.
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69049113666
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Heating the reaction with N-tosyl carbamate substrates to 65°C also promoted reactivity; however, the yields were lower, and inconsistent results were observed.
-
Heating the reaction with N-tosyl carbamate substrates to 65°C also promoted reactivity; however, the yields were lower, and inconsistent results were observed.
-
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-
40
-
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33845217953
-
-
Carboxylic acids have been shown to increase reactivity in oxidative Heck reactions mediated by Pd(II)/bis-sulfoxide, possibly via acid-promoted quinone reoxidation of the metal: (b) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
-
Carboxylic acids have been shown to increase reactivity in oxidative Heck reactions mediated by Pd(II)/bis-sulfoxide, possibly via acid-promoted quinone reoxidation of the metal: (b) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076.
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(c) Delcamp, J. H.; Brucks, A. P.; White, M. C. J. Am. Chem. Soc. 2008, 130, 11270.
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Eur. Pat. 1050531
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For specific reaction conditions see: (b) Anada, M.; Tanaka, M.; Washio, T.; Yamawaki, M.; Abe, T.; Hashimoto, S. Org. Lett. 2007, 9, 4559.
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For previous asymmetric syntheses see: (a) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594.
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