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Volumn 68, Issue 11, 2003, Pages 4355-4360

Lewis acid mediated reactions of zirconacyclopentenes with aldehydes affording homoallyl ketones via Oppenauer-type oxidation

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; CHEMICAL BONDS; DEUTERIUM; ETHYLENE; KETONES;

EID: 0038102454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034107r     Document Type: Article
Times cited : (34)

References (36)
  • 10
    • 0003441992 scopus 로고    scopus 로고
    • Yamamoto, H., Ed.; Wiley-VCH: Weinheim
    • (b) Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, 2000.
    • (2000) Lewis Acids in Organic Synthesis
  • 24
    • 0001281205 scopus 로고
    • Zheng, B.; Srebnik, M. J. Org. Chem. 1995, 60, 3278. See also: Deloux, L.; Srebnik, M. J. Org. Chem. 1994, 59, 6871.
    • (1995) J. Org. Chem. , vol.60 , pp. 3278
    • Zheng, B.1    Srebnik, M.2
  • 25
    • 0001432298 scopus 로고
    • Zheng, B.; Srebnik, M. J. Org. Chem. 1995, 60, 3278. See also: Deloux, L.; Srebnik, M. J. Org. Chem. 1994, 59, 6871.
    • (1994) J. Org. Chem. , vol.59 , pp. 6871
    • Deloux, L.1    Srebnik, M.2
  • 29
    • 0027533983 scopus 로고
    • For preparation of zirconacyclopentenes, see: (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687. (b) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444. (c) Takahashi, T.; Xi, C.; Xi, Z.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 687
    • Takahashi, T.1    Kageyama, M.2    Denisov, V.3    Hara, R.4    Negishi, E.5
  • 30
    • 0000086734 scopus 로고
    • For preparation of zirconacyclopentenes, see: (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687. (b) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444. (c) Takahashi, T.; Xi, C.; Xi, Z.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802.
    • (1995) J. Org. Chem. , vol.60 , pp. 4444
    • Xi, Z.1    Hara, R.2    Takahashi, T.3
  • 31
    • 0001230410 scopus 로고    scopus 로고
    • For preparation of zirconacyclopentenes, see: (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687. (b) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444. (c) Takahashi, T.; Xi, C.; Xi, Z.; Kageyama, M.; Fischer, R.; Nakajima, K.; Negishi, E. J. Org. Chem. 1998, 63, 6802.
    • (1998) J. Org. Chem. , vol.63 , pp. 6802
    • Takahashi, T.1    Xi, C.2    Xi, Z.3    Kageyama, M.4    Fischer, R.5    Nakajima, K.6    Negishi, E.7
  • 34
    • 0037756257 scopus 로고    scopus 로고
    • note
    • It has been reported (refs 12a and 13a) that when a zirconacyclopentene is treated with an aldehyde at 50 °C, a five-membered oxazirconacyclopentene is formed along with release of ethylene. However, if a zirconacyclopentene is treated with an aldehyde at room temperature or 0 °C, a seven-membered oxazirconacycle is formed via insertion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.