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Volumn 12, Issue 2, 2005, Pages 510-517

Synthesis of the indene, THF, and pyrrolidine skeletons by lewis acid mediated cycloaddition of methylenecyclopropanes with aldehydes, N-tosyl aldimines, and acetals

Author keywords

Cycloaddition; Indene; Methylenecyclopropanes; Synthetic methods; THF

Indexed keywords

ALDEHYDES; AMINES; DEUTERIUM; MOLECULAR STRUCTURE; REACTION KINETICS;

EID: 29544440178     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500447     Document Type: Article
Times cited : (65)

References (82)
  • 1
    • 0001487604 scopus 로고    scopus 로고
    • For the synthesis of MCPs see: a) A. Brandi, A. Goti, Chem. Rev. 1998, 98, 589-635;
    • (1998) Chem. Rev. , vol.98 , pp. 589-635
    • Brandi, A.1    Goti, A.2
  • 20
    • 0035794939 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1298-1300.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1298-1300
  • 22
    • 0037420778 scopus 로고    scopus 로고
    • For the Lewis acid mediated cycloaddition of MCPs with activated ketones or aldehydes see: a) M. Shi, B. Xu, Tetrahedron Lett. 2003, 44, 3839-3842;
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3839-3842
    • Shi, M.1    Xu, B.2
  • 23
    • 0037024163 scopus 로고    scopus 로고
    • 2-mediated ring expansions of methylenecyclopropyl amides and imides see: b) M. Lautens, W. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316;
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6312-6316
    • Lautens, M.1    Han, W.2
  • 26
    • 33751554335 scopus 로고
    • for the cycloaddition of gem-dialkoxysubstituted MCPs with aldehydes and imines upon heating see: e) S. Yamago, E. Nakamura, J. Org. Chem. 1990, 55, 5553-5555;
    • (1990) J. Org. Chem. , vol.55 , pp. 5553-5555
    • Yamago, S.1    Nakamura, E.2
  • 36
    • 0000913436 scopus 로고    scopus 로고
    • For some of the Lewis acid or Brønsted acid mediated transformations of MCPs conducted in this laboratory see: a) M. Shi, B. Xu, Org. Lett. 2002, 4, 2145-2148;
    • (2002) Org. Lett. , vol.4 , pp. 2145-2148
    • Shi, M.1    Xu, B.2
  • 52
    • 29544444997 scopus 로고    scopus 로고
    • 000 = 616; diffractometer: Rigaku AFC7R; residuals: R/wR: 0.0882/0.2680. CCDC-210597 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_,request/cif.
  • 53
    • 29544439697 scopus 로고    scopus 로고
    • 000 = 728; diffractometer: Rigaku AFC7R; residuals: R/wR: 0.0545/0.1228. CCDC-210599 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_ request/cif.
  • 57
    • 10044228734 scopus 로고    scopus 로고
    • d) G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esterves, Q. Wang, G. Rasul, G. A. Olah, J. Am. Chem. Soc. 2004, 126, 15770-15776; the reaction of MCP la with benzaldehyde 2a in anhydrous dichloromethane was also studied by bubbling boron trifluoride from a cylinder into the reaction solution by the means of a Schlenk tube, under an argon atmosphere. The reaction proceeded slowly under these reaction conditions; however, when the reaction solution was exposed to the ambient atmosphere the reaction proceeded smoothly to give the cycloaddition products in good yields.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15770-15776
    • Prakash, G.K.S.1    Mathew, T.2    Hoole, D.3    Esterves, P.M.4    Wang, Q.5    Rasul, G.6    Olah, G.A.7
  • 71
    • 0003791302 scopus 로고    scopus 로고
    • Plenum Press, New York
    • It is reasonable to assume that the electron-donating substituents on the double bond can further stabilize the cation see: F. A. Carey, R. J. Sundberg in Advanced Organic Chemistry, 5th ed., Plenum Press, New York, 1998, p. 221 and 419.
    • (1998) Advanced Organic Chemistry, 5th Ed. , pp. 221
    • Carey, F.A.1    Sundberg, R.J.2
  • 76
    • 0001382599 scopus 로고
    • (Eds.: G. A. Olah, P. von R. Schleyer), Wiley, New York
    • a) J. L. Fry, G. J. Karabatsos, in Carbonium Ions, Vol. II (Eds.: G. A. Olah, P. von R. Schleyer), Wiley, New York, 1970, pp. 521;
    • (1970) Carbonium Ions , vol.2 , pp. 521
    • Fry, J.L.1    Karabatsos, G.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.