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Volumn , Issue 7, 2010, Pages 1307-1313

Synthesis of 3-methylenecyclohexan-1-ols by lewis acid catalyzed cyclization of (epoxy-allyl)silanes

Author keywords

Cyclization; Epoxides; Lewis acid catalysis; Lewis acids; Silanes

Indexed keywords


EID: 77149171457     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901263     Document Type: Article
Times cited : (5)

References (40)
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    • For the silylcupration of allenes, see: a
    • For the silylcupration of allenes, see: a) A. Barbero, F. J. Pulido, Acc. Chem. Res. 2004, 37, 817-825;
    • (2004) Acc. Chem. Res , vol.37 , pp. 817-825
    • Barbero, A.1    Pulido, F.J.2
  • 19
    • 27744450298 scopus 로고    scopus 로고
    • For the stannylcupration of allenes, see: a
    • For the stannylcupration of allenes, see: a) A. Barbero, F. J. Pulido, Chem. Soc. Rev. 2005, 34, 913-920;
    • (2005) Chem. Soc. Rev , vol.34 , pp. 913-920
    • Barbero, A.1    Pulido, F.J.2
  • 26
    • 77149128575 scopus 로고    scopus 로고
    • We were not able to isolate or detect aldehydes resulting from isomerization of the starting (epoxy-allyl)silane
    • We were not able to isolate or detect aldehydes resulting from isomerization of the starting (epoxy-allyl)silane.
  • 31
    • 77149126314 scopus 로고    scopus 로고
    • B. Rickborn in Comprehensive Organic Synthesis Carbon-Carbon α-Bond Formation (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, 3, p. 733.
    • b) B. Rickborn in Comprehensive Organic Synthesis Carbon-Carbon α-Bond Formation (Ed.: G. Pattenden), Pergamon Press, Oxford, 1991, vol. 3, p. 733.
  • 34
    • 0001373492 scopus 로고    scopus 로고
    • Products of epoxide rearrangement have been obtained in a similar cyclization reaction: X.-Y. Xiao, S.-K. Park, G. D. Prestwich, J. Org. Chem. 1988, 53, 4869-4872.
    • Products of epoxide rearrangement have been obtained in a similar cyclization reaction: X.-Y. Xiao, S.-K. Park, G. D. Prestwich, J. Org. Chem. 1988, 53, 4869-4872.
  • 38
    • 77149131762 scopus 로고    scopus 로고
    • None of the direct 5-exo or 6-endo epoxy-cyclization products (see Scheme 4) were observed.
    • None of the direct 5-exo or 6-endo epoxy-cyclization products (see Scheme 4) were observed.
  • 39
    • 77149168370 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone,M. Cossi, R. Cammi, B.Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98 (Revision A.7, Gaussian, Inc, Pittsburgh, PA, 1998. Theoretical level: MP2(fc)/3-21G*//HF/3-21G*
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone,M. Cossi, R. Cammi, B.Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98 (Revision A.7), Gaussian, Inc., Pittsburgh, PA, 1998. Theoretical level: MP2(fc)/3-21G*//HF/3-21G*.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.