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Volumn 73, Issue 7, 2008, Pages 2641-2648

Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CYCLOADDITION; KETONES; NICKEL; REACTION KINETICS;

EID: 41649092102     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702508w     Document Type: Article
Times cited : (78)

References (88)
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    • Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon Press: Oxford, UK
    • (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1129-1162.
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    • (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L., Eds.; Pergamon Press: Oxford, UK, 1995; Vol. 12, pp 741-770.
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    • Grotjahn, D.B.1
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    • Recent reports: (b) Gandon, V.; Leca, D.; Aechter, T.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Org. Lett. 2004, 6, 3405.
    • Recent reports: (b) Gandon, V.; Leca, D.; Aechter, T.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Org. Lett. 2004, 6, 3405.
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    • Recent reports: (a) Tanaka, K.; Wada, A.; Noguchi, K. Org. Lett. 2005, 7, 4737.
    • Recent reports: (a) Tanaka, K.; Wada, A.; Noguchi, K. Org. Lett. 2005, 7, 4737.
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    • Recent reports: (b) Bonaga, L. V. R.; Zhang, H. C.; Moretto, A. F.; Ye, H.; Gauthier, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
    • Recent reports: (b) Bonaga, L. V. R.; Zhang, H. C.; Moretto, A. F.; Ye, H.; Gauthier, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473.
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    • C-N reductive elimination: (f) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
    • C-N reductive elimination: (f) Koo, K.; Hillhouse, G. L. Organometallics 1995, 14, 4421.
  • 54
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    • ItBu = 1,3-di-tert-butylimidazol-2-ylidene; IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; IPr = 1,3-bis(2,6- diisopropylphenyl)-imidazol-2-ylidene; SIPr = 1,3-bis(2,6-diisopropylphenyl)-4, 5-dihydroimidazolin-2-ylidene.
    • ItBu = 1,3-di-tert-butylimidazol-2-ylidene; IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene; IPr = 1,3-bis(2,6- diisopropylphenyl)-imidazol-2-ylidene; SIPr = 1,3-bis(2,6-diisopropylphenyl)-4, 5-dihydroimidazolin-2-ylidene.
  • 57
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    • The thermal electrocyclic ring opening of fused α-pyrans is common, see: a
    • The thermal electrocyclic ring opening of fused α-pyrans is common, see: (a) Marvell, E. N.; Caple, G.; Gosink, T. A.; Zimmer, G. J. Am. Chem. Soc. 1966, 88, 619.
    • (1966) J. Am. Chem. Soc , vol.88 , pp. 619
    • Marvell, E.N.1    Caple, G.2    Gosink, T.A.3    Zimmer, G.4
  • 61
    • 41649119252 scopus 로고    scopus 로고
    • Some of this work has been previously reported, see ref 7b
    • Some of this work has been previously reported, see ref 7b.
  • 62
    • 41649114435 scopus 로고    scopus 로고
    • In some cases, excess aldehyde was necessary due to competitive NHC-catalyzed aldehyde cyclotrimerization
    • In some cases, excess aldehyde was necessary due to competitive NHC-catalyzed aldehyde cyclotrimerization.
  • 67
    • 41649113412 scopus 로고    scopus 로고
    • The diastereoselectivity of pyran 37 could not be determined by NMR analysis due to the conformation of the ring; pyran 37 possesses a particularly flattened out structure due to the olefin and lacks any 1,3 interations in the NOE analysis. Unfortunately, we were unable to grow suitable crystals for X-ray analysis to determine the structure of pyran 37.
    • The diastereoselectivity of pyran 37 could not be determined by NMR analysis due to the conformation of the ring; pyran 37 possesses a particularly flattened out structure due to the olefin and lacks any 1,3 interations in the NOE analysis. Unfortunately, we were unable to grow suitable crystals for X-ray analysis to determine the structure of pyran 37.
  • 68
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    • See the Supporting Information for complete X-ray analysis
    • See the Supporting Information for complete X-ray analysis.
  • 84
    • 41649100583 scopus 로고    scopus 로고
    • Trost has utilized acetone as a solvent in Ru-catalyzed cycloisomerizations of diynes and does not report any reactivity with the acetone see ref 17d
    • Trost has utilized acetone as a solvent in Ru-catalyzed cycloisomerizations of diynes and does not report any reactivity with the acetone see ref 17d.
  • 85
    • 41649102123 scopus 로고    scopus 로고
    • Without the addition of 3 Å molecular sieves, cyclization reactions gave inconsistent isolated yields of dihydropyran, and yields ranged from 70% to 83%.
    • Without the addition of 3 Å molecular sieves, cyclization reactions gave inconsistent isolated yields of dihydropyran, and yields ranged from 70% to 83%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.