Transition Metal-Catalyzed Cyclopropanation of Alkenes in Water: Catalyst Efficiency and in Situ Generation of the Diazo Reagent

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4531-4533

  Wurz, Ryan P ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

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ARTICLE;

EID: 0037599763     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0270879     Document Type: Article

References (24)

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3. Carbocyclic Three- and Four-Membered Ring Compounds. In Methods of Organic Chemistry (Houben-Weyl); de Meijere, A., Ed.; Verlag; New York, 1997; Vols. E17a,b. Small Ring Compounds in Organic Synthesis VI. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: New York, 2000; Vol. 207.
4. Carbocyclic Three- and Four-Membered Ring Compounds. In Methods of Organic Chemistry (Houben-Weyl); de Meijere, A., Ed.; Verlag; New York, 1997; Vols. E17a,b. Small Ring Compounds in Organic Synthesis VI. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer: New York, 2000; Vol. 207.
5. For an excellent discussion on the hazardous properties of sulfonyl azide reagents, see: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diato Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.
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8. (c) For a recent report on the large scale generation of ethyl diazoacetate and its direct use in solution without isolation in neat form see: Scott, J. W. Organ. Chem. (Abstr. Am. Chem. Soc. Div. Org. Chem.) 2002, 186, 223.
9. For recent reviews on carrying stereoselective transformations in water, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Grieco, P. A., Ed. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (d) Cornils, B.; Hermann, W. A. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Wiley-VCH: New York, 1998.
10. For recent reviews on carrying stereoselective transformations in water, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Grieco, P. A., Ed. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (d) Cornils, B.; Hermann, W. A. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Wiley-VCH: New York, 1998.
11. For recent reviews on carrying stereoselective transformations in water, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Grieco, P. A., Ed. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (d) Cornils, B.; Hermann, W. A. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Wiley-VCH: New York, 1998.
12. For recent reviews on carrying stereoselective transformations in water, see: (a) Lindström, U. M. Chem. Rev. 2002, 102, 2751. (b) Grieco, P. A., Ed. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (d) Cornils, B.; Hermann, W. A. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; Wiley-VCH: New York, 1998.
13. For a water-soluble Ru(II) catalyst, see: Iwasa S.; Takezawa, F.; Tuchiya, Y.; Nishiyama, H. Chem. Commun. 2001, 59.
14. Paulissen, R.; Reimlinger, H.; Hayez, E.; Hubert, A. J., Teyssié, P. Tetrahedron Lett. 1973, 14, 2233.
15. The Rh(II) hexanoate catalyst shows slightly improved yields compared to that of the pivalate when styrene is used as a substrate; see: Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
16. Wynne, D. C.; Olmstead, M. M.; Jessop, P. G. J. Am. Chem. Soc. 2000, 122, 7638.
17. For Co(II) cat. cyclopropanations in 5% aqueous solvents, see: Ikeno, T.; Nishizuka, A.; Sato, M.; Yamada, T. Synlett 2001, 406.
18. (a) Doyle, M. P.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867.
19. (b) Barberis, M.; Lahuerta, P.; Pérez-Prieto, J.; Sanaú, M. Chem. Commun. 2001, 439.
20. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
21. Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647.
22. 4 was not an effective catalyst under these conditions.
23. Nomack, E. B.; Nelson, A. B. Org. Synth. 1964, C. V. 3, 392.
24. 4 solution as the catalyst (see ref 5c). The cyclopropanation proceeds with equal or better yields than those reported in Table 4. See the Supporting Information for details.