Palladium-catalyzed Additions of Silyl-element Bonds to Bicyclopropylidene - A New Access to Bicyclopropyl and Functionally Substituted Cyclopropylidenepropane Derivatives

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3877-3879

  Pohlmann, Tim ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000372322     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006618v     Document Type: Article

References (21)

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4. (a) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem. 1997, 109, 2626; Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
5. (a) Suginome, M.; Nakamura, H.; Ito, Y. Angew. Chem. 1997, 109, 2626; Angew. Chem., Int. Ed. Engl. 1997, 36, 2516.
6. (b) Suginome, M.; Nakamura, H.; Ito, Y. J. Chem. Soc., Chem. Commun. 1996, 2777.
7. Chenard, B. L.; Zyl, C. M. Van. J. Org. Chem. 1986, 51, 3561.
8. For reviews see: (a) de Meijere, A.; Kozhushkov, S. I.; Khlebnikov, A. F. Topics Curr. Chem. 1999, 207, 89.
9. (b) de Meijere, A.; Kozhushkov, S. I. Eur. J. Org. Chem. 2000, in press.
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11. (a) de Meijere, A. Angew. Chem. 1979, 91, 867; Angew. Chem., Int. Ed. Engl. 1979, 18, 809.
12. (a) de Meijere, A. Angew. Chem. 1979, 91, 867; Angew. Chem., Int. Ed. Engl. 1979, 18, 809.
13. (b) Wiberg, K. B. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1987; p 1.
14. Horn, K. A. Chem. Rev. 1995, 95, 1317.
15. Bicyclopropylidene (1) is easily prepared in three simple steps from commercially available methyl cyclopropanecarboxylate; (a) de Meijere, A.; Kozhushkov, S. I.; Spaeth, T.; Zefirov, N. S. J. Org. Chem. 1993, 58, 502.
16. (b) de Meijere, A.; Kozhushkov, S. I.; Spaeth, T. Org. Synth. 2000, 78, in press.
17. Becker, H., Dissertation, Georg-August-Universität Göttingen, 1997.
18. 2 (234.4): C, 51.23; H, 8.60. Found: C, 51.51; H, 8.85.
19. 1H NMR spectrum.
20. The Pd-catalyzed addition of trimethylsilyl cyanide to 2-phenylmethylenecyclopropane has been reported to yield a mixture of ring-opening and ring-retention products: cf. Chatani, N.; Takeyusa, T.; Hanafusa, T. Tetrahedron Lett. 1988, 29, 3979.
21. For example, cross-coupling reactions should be possible with compound 13a according to a recently developed protocol, cf. Denmark, S. E.; Wehrli, D.; Choi, J. Y. Org. Lett. 2000, 2491 and references therein. The nitrile group in 13g can easily be transformed to a carboxylic acid, an aldehyde, or an aminomethyl functionality, and these derivatives lend themselves to further elaborations.