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Dyker, G, Ed, Wiley-VCH: Weinheim, Germany, Vols
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(a) Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, Germany, 2005; Vols. 1-3.
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Handbook of C-H Transformations
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4
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For insightful discussion and demonstration, see: a
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For insightful discussion and demonstration, see: (a) Chen, M. S.; White, M. C. Science 2007, 318, 783-787.
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Science
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Chen, M.S.1
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5
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0001485967
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For related oxidations, see: b
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For related oxidations, see: (b) Kim, C.; Chen, K.; Kim, J.; Que, L., Jr J. Am. Chem. Soc. 1997, 119, 5964-5965.
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J. Am. Chem. Soc
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Kim, C.1
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84978590581
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(a) Hofmann, A. W. Ber. 1883, 16, 558-560.
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Hofmann, A.W.1
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7
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44949263573
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(b) Hofmann, A. W. Ber. 1885, 18, 5-23.
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Hofmann, A.W.1
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44949264929
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(c) Hofmann, A. W. Ber. 1885, 18, 109-131.
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Hofmann, A.W.1
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(d) Wolff, M. E. Chem. Rev. 1963, 63, 55-64.
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Chem. Rev
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Wolff, M.E.1
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11
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33947471447
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For classic application of the HLF, see
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(f) For classic application of the HLF, see: Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1668.
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J. Am. Chem. Soc
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Corey, E.J.1
Hertler, W.R.2
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12
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0024332001
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Alanine, A. I. D.; Fishwick, C. W. G.; Szantay, C. Tetrahedron Lett. 1989, 30, 6571-6572.
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Tetrahedron Lett
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Alanine, A.I.D.1
Fishwick, C.W.G.2
Szantay, C.3
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13
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0013571312
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For the closest example of a carbamate being used in an HLF to generate nitrogen-containing heterocycles, see: Dicks, P. F, Glover, S. A, Goosen, A, McCleland, C. W. Tetrahedron 1987, 43, 923-934
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For the closest example of a carbamate being used in an HLF to generate nitrogen-containing heterocycles, see: Dicks, P. F.; Glover, S. A.; Goosen, A.; McCleland, C. W. Tetrahedron 1987, 43, 923-934.
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14
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44949111024
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Using menthol carbamate (19, the photolysis reaction can be replaced by thermal conditions (PhCF3, 0.1 equiv of AIBN, 70°C, 5 min) to provide a similar yield of 1,3-diol, without requiring the use of CBr 4
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4.
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15
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33746108032
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For HLF-based 1,5-hydrogen abstraction using a trifluoroacetamide, see: Reddy, L. R.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2006, 8, 2819-2821.
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For HLF-based 1,5-hydrogen abstraction using a trifluoroacetamide, see: Reddy, L. R.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2006, 8, 2819-2821.
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16
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0001101481
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For alternate methods to increase the electrophicity of N-centered radicals, see: a
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For alternate methods to increase the electrophicity of N-centered radicals, see: (a) Johnson, R. A.; Greene, F. D. J. Org. Chem. 1975, 40, 2192-2196.
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J. Org. Chem
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Johnson, R.A.1
Greene, F.D.2
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17
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17844372708
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(b) Chen, Q.; Shen, M.; Tang, Y.; Li, C. Org. Lett. 2005, 7, 1625-1627.
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Org. Lett
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Chen, Q.1
Shen, M.2
Tang, Y.3
Li, C.4
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18
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34547691252
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(c) Francisco, C. G.; Herrera, A. J.; Martín, Á.; Pérez-Martín, I.; Suárez, E. Tetrahedron Lett. 2007, 48, 6384-6388.
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(2007)
Tetrahedron Lett
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Francisco, C.G.1
Herrera, A.J.2
Martín, A.3
Pérez-Martín, I.4
Suárez, E.5
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19
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44949206157
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3 was required.
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3 was required.
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20
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0039366726
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Isolation of isopulegol hydrate: Nishimura, H.; Kaku, K.; Nakamura, T.; Fukazawa, Y.; Mizutani, J. Agric. Biol. Chem. 1982, 46, 319-320.
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Isolation of isopulegol hydrate: Nishimura, H.; Kaku, K.; Nakamura, T.; Fukazawa, Y.; Mizutani, J. Agric. Biol. Chem. 1982, 46, 319-320.
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21
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44949188068
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Isopulegol hydrate is commercially available; however, it has been synthesized many times in from 1 to 5 steps and 4.8 to 35% yield as mixtures of regioisomers. See Supporting Information for a full reference list.
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Isopulegol hydrate is commercially available; however, it has been synthesized many times in from 1 to 5 steps and 4.8 to 35% yield as mixtures of regioisomers. See Supporting Information for a full reference list.
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22
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85008106373
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Isolation of 1,5-diphenyl-1,3-pentanediol: Niwa, M.; Jiang, P.-F.; Hirata, Y. Chem. Pharm. Bull. 1987, 35, 108-111.
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Isolation of 1,5-diphenyl-1,3-pentanediol: Niwa, M.; Jiang, P.-F.; Hirata, Y. Chem. Pharm. Bull. 1987, 35, 108-111.
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23
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0011754220
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For previous syntheses of 1,5-diphenyl-1,3-pentanediol, see ref 12 and: McDougal, P. G, Rico, J. G. Tetrahedron Lett. 1984, 25, 5977-5980
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For previous syntheses of 1,5-diphenyl-1,3-pentanediol, see ref 12 and: McDougal, P. G.; Rico, J. G. Tetrahedron Lett. 1984, 25, 5977-5980.
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24
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44949165188
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Olefins react with acetyl hypobromite before bromination of the carbamate can occur
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Olefins react with acetyl hypobromite before bromination of the carbamate can occur.
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25
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33749509027
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Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634-12635.
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J. Am. Chem. Soc
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Chen, X.1
Goodhue, C.E.2
Yu, J.-Q.3
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26
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0031789377
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Rahman, A.-u.; Yaqoob, M.; Farooq, A.; Anjum, S.; Asif, F.; Choudhary, M. I. J. Nat. Prod. 1998, 61, 1340-1342.
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J. Nat. Prod
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Rahman, A.-U.1
Yaqoob, M.2
Farooq, A.3
Anjum, S.4
Asif, F.5
Choudhary, M.I.6
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27
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0021738437
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Isolation of rengyol (24) and isorengyol (25): Endo, K.; Hikino, H. Can. J. Chem. 1984, 62, 2011-2014.
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Isolation of rengyol (24) and isorengyol (25): Endo, K.; Hikino, H. Can. J. Chem. 1984, 62, 2011-2014.
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28
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0010975430
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Previous syntheses of rengyol (24) and isorengyol (25): (a) Honzumi, M.; Kamikubo, T.; Ogasawara, K. Synlett 1998, 1001-1003.
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Previous syntheses of rengyol (24) and isorengyol (25): (a) Honzumi, M.; Kamikubo, T.; Ogasawara, K. Synlett 1998, 1001-1003.
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30
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0032496934
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For other examples of highly selective intramolecular C-H oxyfunctionalization reactions, see: a
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For other examples of highly selective intramolecular C-H oxyfunctionalization reactions, see: (a) Yang, D.; Wong, M.-K.; Want, X.-C.; Tang, Y.-C. J. Am. Chem. Soc. 1998, 120, 6611-6612.
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(1998)
J. Am. Chem. Soc
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Yang, D.1
Wong, M.-K.2
Want, X.-C.3
Tang, Y.-C.4
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31
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0043032782
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(b) Wong, M.-K.; Chung, N.-W.; He, L.; Wang, X.-C.; Yan, Z.; Tang, Y. C.; Yang, D. J. Org. Chem. 2003, 68, 6321-6328.
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J. Org. Chem
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Wong, M.-K.1
Chung, N.-W.2
He, L.3
Wang, X.-C.4
Yan, Z.5
Tang, Y.C.6
Yang, D.7
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32
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34447625580
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(c) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez- Martín, I.; Suárez, E. Tetrahedron 2007, 63, 8910-8920.
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(2007)
Tetrahedron
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Francisco, C.G.1
Freire, R.2
Herrera, A.J.3
Pérez- Martín, I.4
Suárez, E.5
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33
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33845183266
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(a) Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749-6757.
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J. Am. Chem. Soc
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Mello, R.1
Fiorentino, M.2
Fusco, C.3
Curci, R.4
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34
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0000680491
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For related examples of oxaziridine mediated C-H oxidation, see: b
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For related examples of oxaziridine mediated C-H oxidation, see: (b) DesMarteau, D. D.; Donadelli, A.; Montanari, V.; Petrov, V. A.; Resnati, G. J. Am. Chem. Soc. 1993, 115, 4897-4898.
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(1993)
J. Am. Chem. Soc
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DesMarteau, D.D.1
Donadelli, A.2
Montanari, V.3
Petrov, V.A.4
Resnati, G.5
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