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Volumn 130, Issue 23, 2008, Pages 7247-7249

1,3-Diol synthesis via controlled, radical-mediated C-H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

EID: 44949086718     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802491q     Document Type: Article
Times cited : (191)

References (35)
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    • (2005) Handbook of C-H Transformations , vol.1-3
  • 4
    • 40949096433 scopus 로고    scopus 로고
    • For insightful discussion and demonstration, see: a
    • For insightful discussion and demonstration, see: (a) Chen, M. S.; White, M. C. Science 2007, 318, 783-787.
    • (2007) Science , vol.318 , pp. 783-787
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    • (a) Hofmann, A. W. Ber. 1883, 16, 558-560.
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    • (c) Hofmann, A. W. Ber. 1885, 18, 109-131.
    • (1885) Ber , vol.18 , pp. 109-131
    • Hofmann, A.W.1
  • 9
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    • 33947471447 scopus 로고
    • For classic application of the HLF, see
    • (f) For classic application of the HLF, see: Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657-1668.
    • (1960) J. Am. Chem. Soc , vol.82 , pp. 1657-1668
    • Corey, E.J.1    Hertler, W.R.2
  • 13
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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
    • 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.
  • 14
    • 44949111024 scopus 로고    scopus 로고
    • 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
    • 4.
  • 15
    • 33746108032 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 16
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    • For alternate methods to increase the electrophicity of N-centered radicals, see: a
    • 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.
    • (1975) J. Org. Chem , vol.40 , pp. 2192-2196
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    • 3 was required.
    • 3 was required.
  • 20
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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.
    • Isolation of isopulegol hydrate: Nishimura, H.; Kaku, K.; Nakamura, T.; Fukazawa, Y.; Mizutani, J. Agric. Biol. Chem. 1982, 46, 319-320.
  • 21
    • 44949188068 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 22
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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.
    • 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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    • 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
    • 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.
  • 24
    • 44949165188 scopus 로고    scopus 로고
    • Olefins react with acetyl hypobromite before bromination of the carbamate can occur
    • Olefins react with acetyl hypobromite before bromination of the carbamate can occur.
  • 27
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    • Isolation of rengyol (24) and isorengyol (25): Endo, K.; Hikino, H. Can. J. Chem. 1984, 62, 2011-2014.
    • Isolation of rengyol (24) and isorengyol (25): Endo, K.; Hikino, H. Can. J. Chem. 1984, 62, 2011-2014.
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    • Previous syntheses of rengyol (24) and isorengyol (25): (a) Honzumi, M.; Kamikubo, T.; Ogasawara, K. Synlett 1998, 1001-1003.
    • Previous syntheses of rengyol (24) and isorengyol (25): (a) Honzumi, M.; Kamikubo, T.; Ogasawara, K. Synlett 1998, 1001-1003.
  • 30
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    • For other examples of highly selective intramolecular C-H oxyfunctionalization reactions, see: a
    • 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.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 6611-6612
    • Yang, D.1    Wong, M.-K.2    Want, X.-C.3    Tang, Y.-C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.