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Volumn 38, Issue 26, 1997, Pages 4587-4590

Lewis acid-promoted addition of methylenecyclopropanes to aldehydes and ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE;

EID: 0030950915     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00981-7     Document Type: Article
Times cited : (24)

References (25)
  • 4
    • 84989452197 scopus 로고
    • (b) Arora, S.; Binger, P. Synthesis, 1974, 801-803. Sternberg, E.; Binger, P. Tetrahedron Lett. 1985, 26, 301-304.
    • (1974) Synthesis , pp. 801-803
    • Arora, S.1    Binger, P.2
  • 6
    • 0000154977 scopus 로고
    • Trost, B. M. Ed.; Pergamon Press: Oxford
    • Reviews on the transition metal-catalyzed [3+2] cycloaddition: (a) Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 5, pp. 1185-1205.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1185-1205
    • Ohta, T.1    Takaya, H.2
  • 12
    • 33751554335 scopus 로고
    • Nakamura et. al. have reported the [3+2] cycloaddition of trimethylenemethanes thermally generated from methylenecyclopropanone acetals to carbonyl compounds and electron-deficient alkenes. (a) Yamago, S.; Nakamura, E. J. Org. Chem. 1990, 55, 5553-5555.
    • (1990) J. Org. Chem. , vol.55 , pp. 5553-5555
    • Yamago, S.1    Nakamura, E.2
  • 14
    • 0028299724 scopus 로고
    • Although Mayr et. al. have reported the reaction of 1a with (p-anisyl)phenylcarbenium tetrachloroborate to give a β-(chloromethyl)allylated product, they have not investigated its synthetic utility. Roth, M.; Schade, C.; Mayr, H. J. Org. Chem. 1994, 59, 169-172.
    • (1994) J. Org. Chem. , vol.59 , pp. 169-172
    • Roth, M.1    Schade, C.2    Mayr, H.3
  • 15
    • 0001290261 scopus 로고
    • Trost, B. M. Ed.; Pergamon Press: Oxford
    • Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 527-561.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 16
    • 0001556010 scopus 로고
    • 2-promoted reaction of 2-chloromethyl-3-trimethylsilyl-1-propene with aldehydes. D'Aniello, F.; Mattii, D.; Taddei, M. Synlett 1993, 119-121.
    • (1993) Synlett , pp. 119-121
    • D'Aniello, F.1    Mattii, D.2    Taddei, M.3
  • 17
    • 0343700425 scopus 로고    scopus 로고
    • note
    • The thermodynamical disadvantage of cycloheptene compared with cyclohexane may decelerate the ring opening of cyclopropane. It is also possible that the stereoelectronic effect as shown in the solvolysis of cyclopropyl derivatives inhibits the ring opening when the intermediary carbenium ion 9 attacks 7 from the exo direction. See ref. 12. We can not provide at present a reasonable explanation for the higher reactivity of 7 than 1b.
  • 22
    • 0342395182 scopus 로고
    • Patai, S., Ed.; John Wiley: New York
    • (b) Reeves, R. L. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; John Wiley: New York, 1966; Vol. 1, pp. 589-593.
    • (1966) The Chemistry of the Carbonyl Group , vol.1 , pp. 589-593
    • Reeves, R.L.1
  • 24
    • 0342829967 scopus 로고    scopus 로고
    • note
    • 4 followed by comparison with the stereo-defined authentic sample. See ref. 14. The relative configuration of 14 was determined by the cyclization of the stereo-defined 13. See ref. 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.