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Volumn 9, Issue 14, 2007, Pages 2693-2696

Formation of five-membered carbocycles by intramolecular palladium-catalyzed ring opening of terf-cyclobutanols

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; PALLADIUM;

EID: 34547469555     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070985q     Document Type: Article
Times cited : (32)

References (31)
  • 2
    • 34547433386 scopus 로고    scopus 로고
    • It is interesting to note, however, that there is a marked difference in their reactivity toward electrophiles; this disparity is attributed primarily to bent bonds of cyclopropanes
    • It is interesting to note, however, that there is a marked difference in their reactivity toward electrophiles; this disparity is attributed primarily to bent bonds of cyclopropanes.
  • 22
    • 34547476328 scopus 로고    scopus 로고
    • We thank Dr. Mary Jane Heeg of our Department for single-crystal X-ray analyses. The X-ray data have been deposited with the Cambridge Structural Database: please refer to CSD nos. 239496 (4a, 239454 (4c, 232508 (19, 232507 (20, 230187 (21, and 232509 22
    • We thank Dr. Mary Jane Heeg of our Department for single-crystal X-ray analyses. The X-ray data have been deposited with the Cambridge Structural Database: please refer to CSD nos. 239496 (4a), 239454 (4c), 232508 (19), 232507 (20), 230187 (21), and 232509 (22).
  • 23
    • 0001339418 scopus 로고    scopus 로고
    • Cf. Siloxycyclopropanes are known to react with arylpalladium cation complexes: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296.
    • Cf. Siloxycyclopropanes are known to react with arylpalladium cation complexes: (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296.
  • 25
    • 0001475275 scopus 로고    scopus 로고
    • For related palladium-catalyzed ring expansion reactions, see: a
    • For related palladium-catalyzed ring expansion reactions, see: (a) Larock, R. C.; Reddy, C. K. Org. Lett. 2000, 2, 3325.
    • (2000) Org. Lett , vol.2 , pp. 3325
    • Larock, R.C.1    Reddy, C.K.2
  • 31
    • 34547487634 scopus 로고    scopus 로고
    • Analogous results were also obtained with the minor cyclobutanone product (structure not shown) from the coupling reaction of 1 and 2 (Scheme 1): no annulation products were obtained from a 3:1 inseparable mixture of the two tert-cyclobutanols, which were prepared by addition of the methyl Grignard reagent.
    • Analogous results were also obtained with the minor cyclobutanone product (structure not shown) from the coupling reaction of 1 and 2 (Scheme 1): no annulation products were obtained from a 3:1 inseparable mixture of the two tert-cyclobutanols, which were prepared by addition of the methyl Grignard reagent.


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