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Volumn 44, Issue 19, 2003, Pages 3839-3842

Lewis acid-catalyzed novel [3+2] cycloaddition of methylenecyclopropanes with activated aldehydes or ketones

Author keywords

Activated ketones and aldehydes; Lewis acids; Methylenecyclopropane; 3+2 cycloaddition

Indexed keywords

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; METHYLENECYCLOPROPANE; PROPANE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 0037420778     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00734-2     Document Type: Article
Times cited : (42)

References (23)
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    • For the synthesis of MCPs, see: Brandi A., Goti A. Chem. Rev. 98:1998;589-635.
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  • 3
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    • For reviews, see: (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77; (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
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    • For reviews, see: (a) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77; (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
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    • Lautens, M.1    Klute, W.2    Tam, W.3
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    • and references cited therein
    • For Lewis acid-catalyzed ring-opening reactions of MCPs, see: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145-2148 and references cited therein; (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019-8024; (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 1999, 27, 3045-3048; (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2001, 27, 347-349.
    • (2002) Org. Lett. , vol.4 , pp. 2145-2148
    • Shi, M.1    Xu, B.2
  • 15
    • 0037020647 scopus 로고    scopus 로고
    • For Lewis acid-catalyzed ring-opening reactions of MCPs, see: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145-2148 and references cited therein; (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019-8024; (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 1999, 27, 3045-3048; (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2001, 27, 347-349.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8019-8024
    • Shi, M.1    Chen, Y.2    Xu, B.3    Tang, J.4
  • 16
    • 0033537987 scopus 로고    scopus 로고
    • For Lewis acid-catalyzed ring-opening reactions of MCPs, see: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145-2148 and references cited therein; (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019-8024; (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 1999, 27, 3045-3048; (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2001, 27, 347-349.
    • (1999) Tetrahedron Lett. , vol.27 , pp. 3045-3048
    • Peron, G.L.N.1    Kitteringham, J.2    Kilburn, J.D.3
  • 17
    • 0035825101 scopus 로고    scopus 로고
    • For Lewis acid-catalyzed ring-opening reactions of MCPs, see: (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145-2148 and references cited therein; (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019-8024; (c) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 1999, 27, 3045-3048; (d) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2001, 27, 347-349.
    • (2001) Tetrahedron Lett. , vol.27 , pp. 347-349
    • Peron, G.L.N.1    Norton, D.2    Kitteringham, J.3    Kilburn, J.D.4
  • 18
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    • The crystal structure of 3a has been deposited at the Cambridge Crystallographic Data Center and allocated the deposition numbers CCDC 186571
    • The crystal structure of 3a has been deposited at the Cambridge Crystallographic Data Center and allocated the deposition numbers CCDC 186571.
  • 20
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    • Recently, stepwise [2+2] cycloaddition of ketenes with aldehydes has been disclosed. See:
    • Recently, stepwise [2+2] cycloaddition of ketenes with aldehydes has been disclosed. See: Daniel A.S., Wang Y., Yang H.W., Romo D. Angew. Chem., Int. Ed. 41:2002;1572-1574.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1572-1574
    • Daniel, A.S.1    Wang, Y.2    Yang, H.W.3    Romo, D.4
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  • 23
    • 85031194915 scopus 로고    scopus 로고
    • 3, TMS): δ 13.85, 33.17, 61.98, 68.27, 87.18, 127.14, 127.74, 128.05, 128.47, 129.28, 135.60, 139.80, 140.14, 140.15, 143.05, 168.26; MS (EI):
    • 5: C, 72.61; H, 6.36. Found: C, 72.60; H, 6.51%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.