A highly efficient olefin metathesis initiator: Improved synthesis and reactivity studies

Tetrahedron Letters

Volumn 44, Issue 13, 2003, Pages 2733-2736

  Dunne, Aideen M ^a   Mix, Stefan ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BIPHENYL DERIVATIVE; LIGAND;

ALKYLATION; ARTICLE; CATALYST; ION EXCHANGE CHROMATOGRAPHY; RING CLOSING METATHESIS; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 0037463719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00346-0     Document Type: Article

References (41)

1. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
2. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
3. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
4. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
5. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
6. For recent olefin metathesis reviews, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29; (b) Fürstner, A. Angew. Chem. 2000, 112, 3140-3172; Angew. Chem., Int. Ed. Engl. 2000, 39, 3013-3043; (c) Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529; (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388; (e) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4696; (f) Ivin, K. J. J. Mol. Catal. A 1998, 133, 1-16; (g) Randall, M. L.; Snapper, M. L. J. Mol. Cat. A, 1998, 133, 29-40; (h) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2144; Angew. Chem., Int. Ed. Engl. 1997, 36, 2037-2055.
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40. All products gave satisfactory analytical data.
41. 2 was added 4c (0.0009 mmol). The solution was stirred at rt for 24 h and the solvent removed in vacuo. The residue was purified by column chromatography to give 20 (0.22 mmol, 72%) as a light yellow oil.