메뉴 건너뛰기




Volumn 2, Issue 3, 2000, Pages 281-284

Synthesis of crossed [2 + 2] photocycloadducts: A novel approach to the synthesis of bridged bicyclic alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; BRIDGED COMPOUND;

EID: 0034628258     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991272d     Document Type: Article
Times cited : (29)

References (31)
  • 1
    • 0001485998 scopus 로고
    • and references therein
    • De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359-380 and references therein. Crimmins, M. T. Chem. Rev. 1988, 88, 1453. Crimmins, M. T.; Reinhold: T. L. Organic Reactions; John Wiley and Sons: New York, 1993; Vol. 44, p 297.
    • (1993) Chem. Rev. , vol.93 , pp. 359-380
    • De Keukeleire, D.1    He, S.-L.2
  • 2
    • 33845278846 scopus 로고
    • De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359-380 and references therein. Crimmins, M. T. Chem. Rev. 1988, 88, 1453. Crimmins, M. T.; Reinhold: T. L. Organic Reactions; John Wiley and Sons: New York, 1993; Vol. 44, p 297.
    • (1988) Chem. Rev. , vol.88 , pp. 1453
    • Crimmins, M.T.1
  • 3
    • 0001485998 scopus 로고
    • John Wiley and Sons: New York
    • De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93, 359-380 and references therein. Crimmins, M. T. Chem. Rev. 1988, 88, 1453. Crimmins, M. T.; Reinhold: T. L. Organic Reactions; John Wiley and Sons: New York, 1993; Vol. 44, p 297.
    • (1993) Organic Reactions , vol.44 , pp. 297
    • Crimmins, M.T.1    Reinhold, T.L.2
  • 9
    • 0002497872 scopus 로고
    • For recent discussions of the mechanism of [2 + 2] enone-olefin photocycloadditions, see: Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870-10882. Maradyn, D. J. Weedon, A. C. Tetrahedron Lett. 1994, 35, 8107-8110. Maradyn, D. J. Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359-5360.
    • (1993) Chem. Rev. , vol.93 , pp. 3-22
    • Schuster, D.I.1    Lem, G.2    Kaprinidis, N.A.3
  • 10
    • 0028576984 scopus 로고
    • For recent discussions of the mechanism of [2 + 2] enone-olefin photocycloadditions, see: Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870-10882. Maradyn, D. J. Weedon, A. C. Tetrahedron Lett. 1994, 35, 8107-8110. Maradyn, D. J. Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359-5360.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10870-10882
    • Andrew, D.1    Hastings, D.J.2    Weedon, A.C.3
  • 11
    • 0027969947 scopus 로고
    • For recent discussions of the mechanism of [2 + 2] enone-olefin photocycloadditions, see: Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870-10882. Maradyn, D. J. Weedon, A. C. Tetrahedron Lett. 1994, 35, 8107-8110. Maradyn, D. J. Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359-5360.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 8107-8110
    • Maradyn, D.J.1    Weedon, A.C.2
  • 12
    • 0006775183 scopus 로고
    • For recent discussions of the mechanism of [2 + 2] enone-olefin photocycloadditions, see: Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3-22. Andrew, D.; Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870-10882. Maradyn, D. J. Weedon, A. C. Tetrahedron Lett. 1994, 35, 8107-8110. Maradyn, D. J. Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359-5360.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5359-5360
    • Maradyn, D.J.1    Weedon, A.C.2
  • 13
    • 0039452580 scopus 로고    scopus 로고
    • note
    • Energy minimizations were performed by restricting the distance between the enone carbon and the alkene carbon to 2.5 Å.
  • 15
    • 85088175018 scopus 로고    scopus 로고
    • note
    • 13C NMR and IR. Yields are for isolated, chromatographically purified products.
  • 17
    • 0001855961 scopus 로고    scopus 로고
    • Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 100-110
    • Schwab, P.1    Grubbs, R.H.2    Ziller, J.W.3
  • 18
    • 1542763298 scopus 로고
    • Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 446-452
    • Grubbs, R.H.1    Miller, S.J.2    Fu, G.C.3
  • 19
    • 0000587503 scopus 로고
    • Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7324-7325
    • Fu, G.C.1    Grubbs, R.H.2
  • 24
    • 0042789931 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1993) Chem. Rev. , vol.93 , pp. 2091-2115
    • Dowd, P.1    Zhang, W.2
  • 25
    • 0028814777 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 19-22
    • Rawal, V.H.1    Dufour, C.2    Iwasa, S.3
  • 26
    • 0028954934 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 2729-2732
    • Zheng, W.1    Collins, M.R.2    Mahmood, K.3    Dowd, P.4
  • 27
    • 0028949888 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1995) J. Org. Chem. , vol.60 , pp. 2183-2187
    • Lange, G.L.1
  • 28
    • 0025034013 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1990) Tetrahedron , vol.31 , pp. 5985-5988
    • Lange, G.L.1    Gottardo, C.2
  • 29
    • 0028104212 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1994) Tetrahedron , vol.35 , pp. 8513-8516
    • Lange, G.L.1    Gottardo, C.2
  • 30
    • 37049083735 scopus 로고
    • For an excellent review on radical rearrangements, see: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. See also: Rawal, V. H.; Dufour, C.; Iwasa, S. Tetrahedron Lett. 1995, 36, 19-22. Zheng, W.; Collins, M. R.; Mahmood, K.; Dowd, P.; Tetrahedron Lett. 1995, 36, 2729-2732. Lange, G. L. J. Org. Chem. 1995, 60, 2183-2187, Lange, G. L.; Gottardo, C. Tetrahedron 1990, 31, 5985-5988. Lange, G. L.; Gottardo, C. Tetrahedron 1994, 35, 8513-8516. Ranu, B.; Das, A. R. J. Chem. Soc., Perkin Trans, 1 1994, 921-922.
    • (1994) J. Chem. Soc., Perkin Trans, 1 , pp. 921-922
    • Ranu, B.1    Das, A.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.