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Volumn 47, Issue 52, 2006, Pages 9181-9185

Cyclopropyl carbenoid insertion into alkenylzirconocenes-a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE DERIVATIVE; ALLYL COMPOUND; CARBENOID; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYL CARBENOID; ISONITRILE DERIVATIVE; LITHIUM DERIVATIVE; ORGANOLITHIUM COMPOUND; PROTON; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

EID: 33751171271     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.132     Document Type: Article
Times cited : (22)

References (47)
  • 10
    • 0004258370 scopus 로고
    • Rappoport Z. (Ed), Wiley, New York parts 1 and 2, and 1995, part 3
    • In: Rappoport Z. (Ed). The Chemistry of the Cyclopropyl Group (1987), Wiley, New York parts 1 and 2, and 1995, part 3
    • (1987) The Chemistry of the Cyclopropyl Group
  • 16
    • 0003245764 scopus 로고
    • Stereochemistries of 12 and 14 were assigned by comparison of NMR spectra with known compounds.
    • Stereochemistries of 12 and 14 were assigned by comparison of NMR spectra with known compounds. Schaumann E., Kirschning A., and Narjes F. J. Org. Chem. 56 (1991) 717-723
    • (1991) J. Org. Chem. , vol.56 , pp. 717-723
    • Schaumann, E.1    Kirschning, A.2    Narjes, F.3
  • 18
    • 33751178116 scopus 로고    scopus 로고
    • See Ref. 6b.
  • 19
    • 33751161589 scopus 로고    scopus 로고
    • note
    • * method using Spartan04 for windows (Wavefunction Ltd.).
  • 21
    • 33751184824 scopus 로고    scopus 로고
    • note
    • It is possible that addition occurs by the concerted insertion of the carbenoid into the carbon-zirconium bond with loss of LiBr rather than via an 'ate' complex. Calculations on the structure of the carbenoid show that both the HOMO and LUMO have their major components on the same side as the lithium hence the stereochemical result will be the same as the pathway via an 'ate' complex and would thus have to be taking place via the epimer of 4.
  • 22
    • 33751187475 scopus 로고    scopus 로고
    • note
    • We have not proved the relative stereochemistry between the CH(hexyl)CH(OH)Ph fragment and the cyclohexyl-cyclopropane ring fusion, which can also be viewed as the alkene stereochemistry, but diastereoisomer 37 would only be accessible by the attack of the electrophile anti- to the zirconium, which is unlikely both because the cyclohexyl ring provides an effective steric block, and because it would then be very difficult to account for the syn stereochemistry observed.{A figure is presented}.
  • 23
    • 0034861316 scopus 로고    scopus 로고
    • For example, ozonolysis of alkylidene cyclopropanes is known to be complex and not involve simple cleavage of the double bond:
    • For example, ozonolysis of alkylidene cyclopropanes is known to be complex and not involve simple cleavage of the double bond:. Langler R.F., Raheja R.K., Schank K., and Beck H. Helv. Chim. Acta 84 (2001) 1943-1951
    • (2001) Helv. Chim. Acta , vol.84 , pp. 1943-1951
    • Langler, R.F.1    Raheja, R.K.2    Schank, K.3    Beck, H.4
  • 25
    • 0000010270 scopus 로고
    • The structures of 24-26a and b came from analysis of NMR data and comparisons with similar literature compounds.
    • The structures of 24-26a and b came from analysis of NMR data and comparisons with similar literature compounds. Beruben D., Marek I., Normant J.F., and Platzer N. J. Org. Chem. 60 (1995) 2488-2501
    • (1995) J. Org. Chem. , vol.60 , pp. 2488-2501
    • Beruben, D.1    Marek, I.2    Normant, J.F.3    Platzer, N.4
  • 29
    • 0000104069 scopus 로고    scopus 로고
    • 21 of the methyl and alkene carbons adjacent to the cyclopropyl ring made the relative stereochemistries unambiguous
    • 21 of the methyl and alkene carbons adjacent to the cyclopropyl ring made the relative stereochemistries unambiguous
    • (1996) J. Org. Chem. , vol.61 , pp. 8792-8798
    • Theberge, C.R.1    Verbicky, C.A.2    Zercher, C.K.3
  • 30
    • 33751164104 scopus 로고    scopus 로고
    • note
    • The yield of 28d was consistently very low. The reasonable yield of 28c suggests some activating effect of the phenyl substituent. The low yield of 28e was largely due to the unavoidable bis-insertion of the carbenoid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.