Cyclocarbopalladation: Formation of bicyclic 1,2-cyclobutanediols through a rare 4-exo-dig cyclization

Organic Letters

Volumn 5, Issue 6, 2003, Pages 845-848

  Salem, Bahaâ ^a   Klotz, Philippe ^a   Suffert, Jean ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BROMINE DERIVATIVE; CYCLOBUTANE DERIVATIVE; GAMMA BROMOPROPARGYLIC DIOL; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 0038743685     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0274965     Document Type: Article

References (24)

1. (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
2. (b) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
3. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596
4. (d) Malacria, M. Chem. Rev. 1996, 96, 289-306.
5. (a) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992.
6. (b) de Meijere, A. Chem. Rev. 2000, 100, 2741-3282.
7. (c) Tietze L.; Beifuss, U. Angew. Chem. 1993, 32, 131.
8. (d) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
9. For representative examples, see: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525. (c) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035. (d) Tietze, L.; Kahle, K.; Raschke, T. Chem. Eur. J. 2002, 8, 401.
10. For representative examples, see: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525. (c) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035. (d) Tietze, L.; Kahle, K.; Raschke, T. Chem. Eur. J. 2002, 8, 401.
11. For representative examples, see: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525. (c) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035. (d) Tietze, L.; Kahle, K.; Raschke, T. Chem. Eur. J. 2002, 8, 401.
12. For representative examples, see: (a) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Fretwell, P.; Grigg, R.; Sansano, J. M.; Sridharan, V.; Sukirthalingam, S.; Wilson, D.; Redpath, J. Tetrahedron 2000, 56, 7525. (c) von Zezschwitz, P.; Petry, F.; de Meijere, A. Chem. Eur. J. 2001, 7, 4035. (d) Tietze, L.; Kahle, K.; Raschke, T. Chem. Eur. J. 2002, 8, 401.
13. (a) Burns, B.; Grigg, R.; Sridharan, V.; Worakun, T. Tetrahedron Lett. 1988, 29, 4325.
14. (b) Burns, B.; Grigg, R.; Ratananukul, P.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron Lett. 1988, 29, 5565.
15. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
16. Negishi, E.; Noda, Y.; Lamaty, F.; Vawter, E. Tetrahedron Lett. 1990, 31, 4393.
17. Burns, B.; Grigg, R.; Sridharan, V.; Stevenson, P. Tetrahedron Lett. 1989, 30, 1135.
18. For radical 4-exo-dig cyclization, see: Bogen, S.; Fernsterbank, L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 5037.
19. For an acetylenic alkyllithium 4-exo-dig cyclization, see: Bailey, W. H. ; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080.
20. Suffert, J.; Salem, B.; Klotz, P. J. Am. Chem. Soc. 2001, 123, 12107.
21. 4 (0.1 equiv, 10 mol %), followed by the stannylated reagent (1.3 equiv). The reaction mixture was stirred for 1-17 h in a preheated 90°C oil bath. The reaction was followed by TLC. Then, the reaction mixture was concentrated in vacuo and immediately purified by flash chromatography, leading to the different bicyclic cyclobutan-1,2-diols.
22. (a) Ushida, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1976, 32, 2941-2942.
23. (b) Suffert, J.; Toussaint, D. Tetrahedron Lett. 1997, 38, 5507-5510.
24. See supporting Information of ref 10.