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Volumn 5, Issue 11, 2003, Pages 1855-1858

A stereoselective enyne cross metathesis

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ETHYLENE;

EID: 0042390682     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034408n     Document Type: Article
Times cited : (74)

References (52)
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    • For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (d) Furstner, A. Topics in Organometallics Chemistry; Springer-Verlag: Berlin, Germany, 1998; Vol. 1. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (g) Philips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75. (h) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (i) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Soc. 2001, 34, 18.
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    • 28244440935 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (d) Furstner, A. Topics in Organometallics Chemistry; Springer-Verlag: Berlin, Germany, 1998; Vol. 1. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (g) Philips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75. (h) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (i) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Soc. 2001, 34, 18.
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    • 0001811974 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (d) Furstner, A. Topics in Organometallics Chemistry; Springer-Verlag: Berlin, Germany, 1998; Vol. 1. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (g) Philips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75. (h) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (i) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Soc. 2001, 34, 18.
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    • 0344006321 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (d) Furstner, A. Topics in Organometallics Chemistry; Springer-Verlag: Berlin, Germany, 1998; Vol. 1. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (g) Philips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75. (h) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (i) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Soc. 2001, 34, 18.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3013
    • Furstner, A.1
  • 9
    • 0034746687 scopus 로고    scopus 로고
    • For recent reviews on olefin metathesis, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833. (d) Furstner, A. Topics in Organometallics Chemistry; Springer-Verlag: Berlin, Germany, 1998; Vol. 1. (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413. (f) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (g) Philips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75. (h) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (i) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Soc. 2001, 34, 18.
    • (2001) Acc. Chem. Soc. , vol.34 , pp. 18
    • Trnka, T.M.1    Grubbs, R.H.2
  • 10
    • 0037244612 scopus 로고    scopus 로고
    • For recent reviews on enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (b) Mori, M. Top. Organomet. Chem. 1998, 1 133.
    • (2003) Synthesis , pp. 1
    • Poulsen, C.S.1    Madsen, R.2
  • 11
    • 0000449988 scopus 로고    scopus 로고
    • For recent reviews on enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (b) Mori, M. Top. Organomet. Chem. 1998, 1 133.
    • (1998) Top. Organomet. Chem. , vol.1 , pp. 133
    • Mori, M.1
  • 38
  • 46
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    • note
    • The amount of olefins and the catalyst had to be maintained to that level to drive the cross-metathesis reaction to completion and to minimize the formation of II.
  • 47
    • 0141602075 scopus 로고    scopus 로고
    • note
    • 2 (0.2 mL). Second-generation Grubbs catalyst was added to the reaction mixture at room temperature and the resulting reaction mixture was stirred for 24 h at room temperature under ethylene atmosphere (through balloon attachment) and concentrated under reduced pressure. Then the residue was purified by flash column chromatography on silica gel to afford the desired product.
  • 52
    • 0141490543 scopus 로고    scopus 로고
    • note
    • 2 under ethylene atmosphere for 24 h resulted in only the unreacted starting materials. Allyl butyl ether gave a similar result.


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