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Volumn 10, Issue 16, 2008, Pages 3619-3621

Pd-catalyzed borylative polycyclization of enediynes to allylboronates

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; BIS(PINACOLATO)DIBORON; BORON DERIVATIVE; BORONIC ACID DERIVATIVE; ENEDIYNE; PALLADIUM;

EID: 54049098481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801424m     Document Type: Article
Times cited : (44)

References (36)
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    • Recent examples of synthetic applications of alkyltrifluoroborates: (a) Molander, G. A.; Yokoyama, Y J. Org. Chem. 2006, 71, 2493-2498.
  • 11
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    • Diboration of allenes: (a) Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328-16329.
    • Diboration of allenes: (a) Pelz, N. F.; Woodward, A. R.; Burks, H. E.; Sieber, J. D.; Morken, J. P. J. Am. Chem. Soc. 2004, 126, 16328-16329.
  • 12
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    • Diboration of alkenes: (b) Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702-8703.
    • Diboration of alkenes: (b) Morgan, J. B.; Miller, S. P.; Morken, J. P. J. Am. Chem. Soc. 2003, 125, 8702-8703.
  • 13
    • 27644475970 scopus 로고    scopus 로고
    • Hall, D. G, Ed, Wiley-VCH: Weinheim
    • Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 1-99.
    • (2005) Boronic Acids , pp. 1-99
  • 19
    • 0141988948 scopus 로고    scopus 로고
    • Yang, F.-Y.; Shanmugasundaram, M.; Chuang, S.-Y.; Ku, P.-J.; Wu, M.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2003, 125, 12576-12583. Metal-catalyzed synthesis of allylboronates: (a) Ishiyama, T.; Ahiko, T.; Miyaura, N Tetrahedron Lett. 1996, 37, 6889-6992.
    • Yang, F.-Y.; Shanmugasundaram, M.; Chuang, S.-Y.; Ku, P.-J.; Wu, M.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2003, 125, 12576-12583. Metal-catalyzed synthesis of allylboronates: (a) Ishiyama, T.; Ahiko, T.; Miyaura, N Tetrahedron Lett. 1996, 37, 6889-6992.
  • 20
    • 36849074311 scopus 로고    scopus 로고
    • Enantioselective synthesis: (b) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M J. Am. Chem. Soc. 2007, 129, 14856-14857. See references cited therein.
    • Enantioselective synthesis: (b) Ito, H.; Ito, S.; Sasaki, Y.; Matsuura, K.; Sawamura, M J. Am. Chem. Soc. 2007, 129, 14856-14857. See references cited therein.
  • 23
    • 61349175680 scopus 로고    scopus 로고
    • Silylcarbocyclization of enynes: (a) Lee, S.-Y.; Ojima. I J. Am. Chem. Soc. 2000, 122, 2385-2386.
    • Silylcarbocyclization of enynes: (a) Lee, S.-Y.; Ojima. I J. Am. Chem. Soc. 2000, 122, 2385-2386.
  • 26
    • 61349127005 scopus 로고    scopus 로고
    • Boronates tend to decompose in column chromatography when longer retention times are used, which precludes isolation of pure compounds in some cases
    • Boronates tend to decompose in column chromatography when longer retention times are used, which precludes isolation of pure compounds in some cases.
  • 27
    • 61349121858 scopus 로고    scopus 로고
    • Related enediynes containg terminal alkynes with bis(sulfonyl)-methane or NTs as tethers did not afford the desired compunds
    • Related enediynes containg terminal alkynes with bis(sulfonyl)-methane or NTs as tethers did not afford the desired compunds.
  • 28
    • 61349199970 scopus 로고    scopus 로고
    • The same double-bond configuration was observed in dienes obtained from 1b and 1c (NOESY), although low yields (<15%) were observed in these cases. Partial decomposition of these compounds precludes isolating them in higher yields.
    • The same double-bond configuration was observed in dienes obtained from 1b and 1c (NOESY), although low yields (<15%) were observed in these cases. Partial decomposition of these compounds precludes isolating them in higher yields.
  • 29
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    • Related carbocycles by Rh-catalyzed reactions: Shibata, T.; Kurokawa, H.; Kanda, K J. Org. Chem. 2007, 72, 6521-6525.
    • Related carbocycles by Rh-catalyzed reactions: Shibata, T.; Kurokawa, H.; Kanda, K J. Org. Chem. 2007, 72, 6521-6525.
  • 30
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    • Approximate yield since starting diene 3a(Z) was not pure. These compounds tend to decompose and are difficult to purify.
    • Approximate yield since starting diene 3a(Z) was not pure. These compounds tend to decompose and are difficult to purify.
  • 31
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    • Cycloisomerization of enynes and enediynes: (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
    • Cycloisomerization of enynes and enediynes: (a) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 12491-12509.
  • 33
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    • Probably, the steric hindrance between the phenyl rings precludes oxidation of the benzylic position in 4j.
    • Probably, the steric hindrance between the phenyl rings precludes oxidation of the benzylic position in 4j.
  • 34
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    • Reviews: a, Abel, E. W, Stone, F. G. A, Wilkinson, G, Eds, Pergamon: Oxford, Chapter 8.3
    • Reviews: (a) Oppolzer, W. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 8.3.
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    • Oppolzer, W.1
  • 36
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    • A β-hydrogen elimination involving the exocyclic chain would destroy the stereochemical information contained in the starting alkene
    • A β-hydrogen elimination involving the exocyclic chain would destroy the stereochemical information contained in the starting alkene.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.