Stereoselectivity and stereospecificity of cyclopropanation reactions with stable (phosphanyl)(silyl)carbenes

Journal of the American Chemical Society

Volumn 122, Issue 18, 2000, Pages 4464-4470

  Goumri Magnet, Stéphanie ^a   Kato, Tsuyoshi ^a   Gornitzka, Heinz ^a   Baceiredo, Antoine ^a   Bertrand, Guy ^a  

^a UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(PHOSPHANYL)(SILYL)CARBENE; CARBENE; CYCLOPROPANE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; COMPLEX FORMATION; CRYSTALLIZATION; NUCLEAR MAGNETIC RESONANCE; PHASE TRANSITION; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY; X RAY DIFFRACTION;

EID: 0034630853     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994408b     Document Type: Article

References (41)

1. Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269.
2. (a) Moss, R. A. Acc. Chem. Res. 1989, 22, 15.
3. (b) Minkin, V. I.; Ya Simkin, B.; Glukhovtsev, M. N. Russ. Chem. Rev. 1989, 58, 1067.
4. (c) Regitz, M. Carbene (Carbenoide); Methoden der Organische Chemie (Houben-Weyl); Thieme Verlag: Stuttgart, 1989; Vol. E19b, Parts 1 and 2.
5. (d) de Meijere, A. Carbocyclic Three-Membered Ring Compounds: Methoden der Organische Chemie (Houben-Weyl); Thieme Verlag: Stuttgart, 1996; Vol. E17a.
6. (a) Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411.
7. (b) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
8. (c) Frühauf, H. W. Chem. Rev. 1997, 97, 523.
9. (a) Skell, P. S.; Garner, A. Y. J. Am. Chem. Soc. 1956, 78, 3409 and 5430.
10. (b) Skell, P. S.; Woodworth, R. C. J. Am. Chem. Soc. 1956, 78, 4496 and 6427.
11. (c) Skell, P. S. Tetrahedron 1985, 41, 1427.
12. (d) Gaspar, P. P.; Hammond, G. S. In Carbenes; Moss, R. A., Jones, M., Jr., Eds., Wiley-Interscience: New York, 1973; Vol. II, p 153.
13. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: New York, 1991; Vol. 4.
14. For reviews on stable singlet carbenes see: (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (c) Bourissou, D.; Bertrand, G. Adv. Organomet. Chem. 1999, 44, 175.
15. For reviews on stable singlet carbenes see: (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (c) Bourissou, D.; Bertrand, G. Adv. Organomet. Chem. 1999, 44, 175.
16. For reviews on stable singlet carbenes see: (a) Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39. (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162. (c) Bourissou, D.; Bertrand, G. Adv. Organomet. Chem. 1999, 44, 175.
17. - obtained by reduction of the corresponding stable carbene IIa. According to ESR spectroscopy and ab initio calculations, the additional electron is not located at the carbene carbon atom but delocalized into the PhCN fragment: Enders, D.; Breuer, K.; Raabe, G.; Simonet, J.; Ghanimi, A.; Stegmann, H. B.; Teles, J. H. Tetrahedron Lett. 1997, 38, 2833.
18. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
19. (a) Igau, A.; Baceiredo, A.; Trinquier, G.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 621.
20. (b) Gillette, G. R.; Igau, A.; Baceiredo, A.; Bertrand, G. New J. Chem. 1991, 15, 393.
21. Moss, R. A.; Shea S.; Hadel, L. M.; Kmiecik-Lawrynowicz, G.; Wlostowska, J.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1987, 109, 4341.
22. (a) Igau, A.; Grützmacher, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1988, 110, 6463.
23. (b) Alcaraz, G.; Reed, R.; Baceiredo, A.; Bertrand, G. J. Chem. Soc., Chem. Commun. 1993, 1354.
24. Spectroscopic Methods in Organic Chemistry; Hesse, M., Meier, H., Zeeh, B., Eds; Georg Thieme Verlag: Stuttgart, 1997; pp 202-204.
25. The stereochemical results are most compatible with concerted addition of 1a to styrene, in accord with typical singlet carbene behavior, and with the lack of theoretical prohibition of concerted nucleophilic carbene-olefin [1+2] cycloadditions. However, there is no spin-inversion barrier to rapid closure of a 1,3-dipole, so that a two-step singlet carbene addition is not as certain to occur nonstereospecifically as in a triplet carbene addition, which proceeds via a triplet 1,3-diradical. Moss, R. A.; Huselton, J. K. J. Chem. Soc., Chem. Commun. 1976, 950.
26. (a) Nguyen, M. T.; McGinn, M. A.; Hegarty, A. F. Inorg. Chem. 1986, 25, 2185.
27. (b) Hoffmann, M. R.; Kuhler, K. J. Chem. Phys. 1991, 94, 8029.
28. (c) Dixon, D. A.; Dobbs, K. B.; Arduengo, A. J., III; Bertrand, G. J. Am. Chem. Soc. 1991, 113, 8782.
29. (d) Nyulaszi, L.; Szieberth, D.; Reffy, J.; Veszpremi, T. J. Mol. Struct. (THEOCHEM) 1998, 453, 91.
30. Goumri-Magnet, S.; Polishchuk, O.; Gornitzka, H.; Marsden, C. J.; Baceiredo, A.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 3727.
31. Diaz-Requejo, M. M.; Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1997, 16, 4399.
32. Sheridan, R. S.; Moss, R. A.; Wilk, B. K.; Shen, S.; Wlostowski, M.; Kesselmayer, M. A.; Subramanian, R.; Kmiecik-Lawrynowicz, G.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1988, 110, 7563.
33. Dunn, J. A.; Pezacki, J. P.; McGlinchey, M. J.; Warkentin, J. J. Org. Chem. 1999, 64, 4344 and references therein.
34. (a) Keating, A. E.; Merrigan, S. R.; Singleton, D. A.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3933.
35. (b) Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770.
36. "Endo rule": Woodward, R. B.; Hoffmann, R. The conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1971.
37. Regitz, M.; Heydt, H. In 1,3-Dipolar Cycloadditian Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 393-558.
38. See, for example: Brahms, D. L. S.; Dailey, W. P. Chem. Rev. 1996, 96, 1585.
39. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, 46, 467.
40. Sheldrick, G. M., SHELXL-97, Program for Crystal Structure Refinement, Universität Gottingen, 1997.
41. Flack, H. D. Acta Cryslallogr. Sect. A 1983, 39, 876.