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Volumn 121, Issue 42, 1999, Pages 9895-9896

Asymmetric cyclopentannelation. Axial to tetrahedral chirality transfer [13]

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPENTANE; ETHER DERIVATIVE; NATURAL PRODUCT;

EID: 0033610446     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992669f     Document Type: Letter
Times cited : (56)

References (23)
  • 7
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    • (g) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J.-B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438-3442. For related work involving Nazarov cyclizations of allenyl ketones see: Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494. For related work, see: Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Tetrahedron Lett. 1988, 29, 6865, et seq.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3438-3442
    • Tius, M.A.1    Astrab, D.P.2    Fauq, A.H.3    Ousset, J.-B.4    Trehan, S.5
  • 8
    • 0032497668 scopus 로고    scopus 로고
    • (g) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J.-B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438-3442. For related work involving Nazarov cyclizations of allenyl ketones see: Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494. For related work, see: Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Tetrahedron Lett. 1988, 29, 6865, et seq.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7491-7494
    • Hashmi, A.S.K.1    Bats, J.W.2    Choi, J.-H.3    Schwarz, L.4
  • 9
    • 0001318688 scopus 로고
    • et seq.
    • (g) Tius, M. A.; Astrab, D. P.; Fauq, A. H.; Ousset, J.-B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438-3442. For related work involving Nazarov cyclizations of allenyl ketones see: Hashmi, A. S. K.; Bats, J. W.; Choi, J.-H.; Schwarz, L. Tetrahedron Lett. 1998, 39, 7491-7494. For related work, see: Jacobi, P. A.; Armacost, L. M.; Kravitz, J. I.; Martinelli, M. J.; Selnick, H. G. Tetrahedron Lett. 1988, 29, 6865, et seq.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6865
    • Jacobi, P.A.1    Armacost, L.M.2    Kravitz, J.I.3    Martinelli, M.J.4    Selnick, H.G.5
  • 11
    • 13044308712 scopus 로고    scopus 로고
    • note
    • Had the cyclization of 1 to 3 not taken place spontaneously under mild conditions, the kinetic preference for the formation of 3 would not have been detected, since isomerization would have certainly been rapid under the conditions of a conventional acid-catalyzed Nazarov reaction.
  • 13
    • 0012760680 scopus 로고
    • Morel-Fourrier, C.; Dulcere, J.-P.; Santelli, M. J. Am. Chem. Soc. 1991, 113, 8062-8069. Motoyoshiya, J.; Yazaki, T.; Hayashi, S. J. Org. Chem. 1991, 56, 735-740.
    • (1991) J. Org. Chem. , vol.56 , pp. 735-740
    • Motoyoshiya, J.1    Yazaki, T.2    Hayashi, S.3
  • 14
    • 0030968142 scopus 로고    scopus 로고
    • For leading references, see: Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858-860. See also: Noguchi, Y.; Takiyama, H.; Kalsuki, T. Synlett 1998, 543-545. Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49-56.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 858-860
    • Mikami, K.1    Yoshida, A.2
  • 15
    • 0000378278 scopus 로고    scopus 로고
    • For leading references, see: Mikami, K.; Yoshida, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 858-860. See also: Noguchi, Y.; Takiyama, H.; Kalsuki, T. Synlett 1998, 543-545. Alexakis, A.; Mangeney, P.; Ghribi, A.; Marek, I.; Sedrani, R.; Guir, C.; Normant, J. F. Pure Appl. Chem. 1983, 60, 49-56.
    • (1998) Synlett , pp. 543-545
    • Noguchi, Y.1    Takiyama, H.2    Kalsuki, T.3
  • 19
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    • Vinyllithium 11 was generated by metal-halogen exchange from the iodide. See: Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834-5845. Le Noble, W. J. J. Am. Chem. Soc. 1961, 83, 3897-3899. Terrel, L. R.; Ward, J. S., III; Maleczka, R. E., Jr. Tetrahedron Lett. 1999, 40, 3097-3100.
    • (1991) J. Org. Chem. , vol.56 , pp. 5834-5845
    • Chen, S.-H.1    Horvath, R.F.2    Joglar, J.3    Fisher, M.J.4    Danishefsky, S.J.5
  • 20
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    • Vinyllithium 11 was generated by metal-halogen exchange from the iodide. See: Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834-5845. Le Noble, W. J. J. Am. Chem. Soc. 1961, 83, 3897-3899. Terrel, L. R.; Ward, J. S., III; Maleczka, R. E., Jr. Tetrahedron Lett. 1999, 40, 3097-3100.
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 3897-3899
    • Le Noble, W.J.1
  • 21
    • 0033574567 scopus 로고    scopus 로고
    • Vinyllithium 11 was generated by metal-halogen exchange from the iodide. See: Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834-5845. Le Noble, W. J. J. Am. Chem. Soc. 1961, 83, 3897-3899. Terrel, L. R.; Ward, J. S., III; Maleczka, R. E., Jr. Tetrahedron Lett. 1999, 40, 3097-3100.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3097-3100
    • Terrel, L.R.1    Ward III, J.S.2    Maleczka Jr., R.E.3


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