The preparation of a bridgehead organolithium reagent

Synlett

Volumn , Issue 4, 2003, Pages 497-500

  Harmata, Michael ^a   Kirchhoefer, Patrick ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

Cycloadditions; Electrophilic additions; Lithium; Metalations; Metathesis

Indexed keywords

BRIDGED COMPOUND; ORGANOLITHIUM COMPOUND; REAGENT;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLOADDITION; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037243534     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37521     Document Type: Article

References (19)

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2. For examples, see: Wieringa, J. H.; Strating, J.; Wynberg, H. Synth. Commun. 1972, 2, 191. (b) Molle, G.; Bauer, P.; Dubois, J. E. J. Org. Chem. 1983, 48, 2975. (c) Kraus, G. A.; Siclovan, T. M. J. Org. Chem. 1994, 59, 922. (d) Wender, P. A.; Wesjohann, L. A.; Peschke, B.; Rawlins, D. B. Tetrehedron Lett. 1995, 36, 7181.
3. For examples, see: Wieringa, J. H.; Strating, J.; Wynberg, H. Synth. Commun. 1972, 2, 191. (b) Molle, G.; Bauer, P.; Dubois, J. E. J. Org. Chem. 1983, 48, 2975. (c) Kraus, G. A.; Siclovan, T. M. J. Org. Chem. 1994, 59, 922. (d) Wender, P. A.; Wesjohann, L. A.; Peschke, B.; Rawlins, D. B. Tetrehedron Lett. 1995, 36, 7181.
4. For examples, see: Wieringa, J. H.; Strating, J.; Wynberg, H. Synth. Commun. 1972, 2, 191. (b) Molle, G.; Bauer, P.; Dubois, J. E. J. Org. Chem. 1983, 48, 2975. (c) Kraus, G. A.; Siclovan, T. M. J. Org. Chem. 1994, 59, 922. (d) Wender, P. A.; Wesjohann, L. A.; Peschke, B.; Rawlins, D. B. Tetrehedron Lett. 1995, 36, 7181.
5. Harmata, M.; Shao, L. Synthesis 1999, 1534.
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12. Bokesch, H. R.; McKee, T. C.; Cardellina, J. H. II; Boyd, M. R. Tetrahedron Lett. 1996, 37, 3259.
13. CCDC 200258 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].
14. 3a and: Wright, D. L.; Usher, L. C.; Estrella-Jimenez, M. Org. Lett. 2001, 3, 4275.
15. 13C and IR spectral data as well as satisfactory combustion analysis.
16. For the formation of 1 see: Folkins, P. L.; Harpp, D. N. J. Org. Chem. 1992, 57, 2013.
17. 4, filtered, and concentrated. The crude yellow oil was purified by column chromatography (5% EtOAc-hexanes) to give separable 4 and 5 (2.18 g, 86% for 2 steps) as a crystalline solid.
18. 4: C, 74.56; H, 8.16. Found: C, 74.56; H, 8.30.
19. 3: C 74.45; H, 9.02. Found: C, 74.59; H, 8.88.