Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2785-2788

  Aggarwal, Varinder K ^a   De Vicente, Javier ^a   Bonnert, Roger V ^a,b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001004998     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0164177     Document Type: Article

References (33)

1. For recent reviews, see: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley-Interscience: New York, 1998.
2. (b) Dörwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: New York, 1998.
3. (c) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hedegeus, L. S., Ed.; Pergamon Press: New York, 1995: Vol. 12; Chapters 5.1 and 5.2.
4. (d) Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459.
5. (e) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
6. Apart from diazomethane, diazoalkanes are not usually successful in cyclopropanation, as the metal carbene readily undergoes 1,2-hydrogen shifts to give alkenes: Doyle, M. P.; High, K. G.; Oon, H. S.-M.; Osborn, A. K. Tetrahedron Lett. 1989, 30, 3049. See also ref 1a.
7. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: London, 1996.
8. Doyle, M. P.; Griffin, J. H.; Bagheri, V.; Dorow, R. L. Organometallics 1984, 3, 53.
9. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem., Int. Ed. 2001, 40, 1430. We have also used this procedure for aziridination of imines and cyclopropanation of electron-deficient alkenes: Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. In addition, this procedure has been utilized for homologation of aldehydes: Aggarwal, V. K.; de Vicente, J.; Pelotier, B.; Holmes, I. H.; Bonnert, R. V. Tetrahedron Lett. 2000, 41, 10327.
10. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem., Int. Ed. 2001, 40, 1430. We have also used this procedure for aziridination of imines and cyclopropanation of electron-deficient alkenes: Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. In addition, this procedure has been utilized for homologation of aldehydes: Aggarwal, V. K.; de Vicente, J.; Pelotier, B.; Holmes, I. H.; Bonnert, R. V. Tetrahedron Lett. 2000, 41, 10327.
11. Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lydon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem., Int. Ed. 2001, 40, 1430. We have also used this procedure for aziridination of imines and cyclopropanation of electron-deficient alkenes: Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. In addition, this procedure has been utilized for homologation of aldehydes: Aggarwal, V. K.; de Vicente, J.; Pelotier, B.; Holmes, I. H.; Bonnert, R. V. Tetrahedron Lett. 2000, 41, 10327.
12. Palladium(II) salts have been used extensively in the cyclopropanation of electron-deficient alkenes with diazomethane: Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375 and references therein. They have also occasionally been employed in cyclopropanation of electron-rich alkenes with ethyl diazoacetate: Miller, K. J.; Baag, J. H.; Abu-Omar, M. M. Inorg. Chem. 1999, 38, 4510 and references therein. However, there are only sporadic examples of the use of Pd(0) in cyclopropanation: Nakamura, A.; Koyama, T.; Otsuka, S. Bull. Chem. Soc. Jpn. 1978, 51, 593. Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
13. Palladium(II) salts have been used extensively in the cyclopropanation of electron-deficient alkenes with diazomethane: Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375 and references therein. They have also occasionally been employed in cyclopropanation of electron-rich alkenes with ethyl diazoacetate: Miller, K. J.; Baag, J. H.; Abu-Omar, M. M. Inorg. Chem. 1999, 38, 4510 and references therein. However, there are only sporadic examples of the use of Pd(0) in cyclopropanation: Nakamura, A.; Koyama, T.; Otsuka, S. Bull. Chem. Soc. Jpn. 1978, 51, 593. Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
14. Palladium(II) salts have been used extensively in the cyclopropanation of electron-deficient alkenes with diazomethane: Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375 and references therein. They have also occasionally been employed in cyclopropanation of electron-rich alkenes with ethyl diazoacetate: Miller, K. J.; Baag, J. H.; Abu-Omar, M. M. Inorg. Chem. 1999, 38, 4510 and references therein. However, there are only sporadic examples of the use of Pd(0) in cyclopropanation: Nakamura, A.; Koyama, T.; Otsuka, S. Bull. Chem. Soc. Jpn. 1978, 51, 593. Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
15. Palladium(II) salts have been used extensively in the cyclopropanation of electron-deficient alkenes with diazomethane: Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375 and references therein. They have also occasionally been employed in cyclopropanation of electron-rich alkenes with ethyl diazoacetate: Miller, K. J.; Baag, J. H.; Abu-Omar, M. M. Inorg. Chem. 1999, 38, 4510 and references therein. However, there are only sporadic examples of the use of Pd(0) in cyclopropanation: Nakamura, A.; Koyama, T.; Otsuka, S. Bull. Chem. Soc. Jpn. 1978, 51, 593. Anciaux, A. J.; Hubert, A. J.; Noels, A. F.; Petiniot, N.; Teyssié, P. J. Org. Chem. 1980, 45, 695.
16. 10 hence the low yield with dihydropyran (entry 2).
17. 4
18. trans). The relative stereochemistry of cis- and trans-2-isopropenyl-2-methyl-1-phenylcyclopropane (entries 11 and 12, Table 2) was also confirmed by NOE experiments.
19. de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547.
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21. 2: Seitz, W. J.; Hossain, M. M. Tetrahedron Lett. 1994, 35, 7561. For a discussion on the mechanism, see ref 1a.
22. Similar diastereoselectivity was originally found by Casey using an electrophilic tungsten phenylcarbene: Casey, C. P.; Polichnowski, S. W.; Shusterman, A. J.; Jones, C. R. J. Am. Chem. Soc. 1979, 101, 7282.
23. None of the reactions presented in Table 3 have been optimized.
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31. Kaiser, C.; Weinstock, J. Org. Synth. 1971, 51, 48.
32. During the course of this work, Pérez described a cis selective cyclopropanation of styrene with ethyl diazoacetate using a copper(I) tris-(pyrazoyl)borate species: Díaz-Requejo, M. M.; Belderaín, T. R.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2001, 123, 3167.
33. 4 catalyst only gave low enantioselectivity.