Stereochemistry of Cyclopropane Formation Involving Group IV Organometallic Complexes

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1699-1704

  Casey, Charles P ^a   Strotman, Neil A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; ORGANOMETALLICS; SYNTHESIS (CHEMICAL); ZIRCONIUM;

RING CLOSURE; TRANSITION STATE STRUCTURES;

STEREOCHEMISTRY;

3 DEUTERO 1 METHYL 2 PHENYL 1 CYCLOPROPANOL; ACETIC ACID ETHYL ESTER; ALCOHOL; AMINE; BETA DEUTEROSTYRENE; BORON; BROMIDE; CHLORINE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; CYCLOPROPYLBENZENE; DEUTERIUM; ETHYL MAGNESIUM BROMIDE; FLUORINE; GRIGNARD REAGENT; MAGNESIUM; METAL COMPLEX; N,N DIMETHYLFORMAMIDE; ORGANOMETALLIC COMPOUND; OXYGEN; PHENYL GROUP; PRASEODYMIUM; PROPANOL; PROPYLAMINE; REAGENT; STYRENE DERIVATIVE; TITANIUM DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG; ZIRCONIUM;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CYCLOPROPANATION; DE MEIJERE REACTION; HYDROXYCYCLOPROPANATION; HYDROXYLATION; KULINKOVICH REACTION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 1242336835     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030436p     Document Type: Article

References (54)

1. de Meijere, A. Chem. Rev. 2003, 103, 931.
2. (a) Pietruszka, J. Chem. Rev. 2003, 103, 1051.
3. (b) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
4. (c) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.
5. (d) Dolbier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071.
6. For recent reviews of cyclopropane formation using early transition metal reagents, see: (a) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789.
7. (b) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
8. (c) Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002; pp 390-434.
9. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
10. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234.
11. (a) Kulinkovich, O. G.; Savchenko, A. I.; Sviridov, S. V.; Vasilevski, D. A. Mendeleev Commun. 1993, 230.
12. (b) Kasatkin, A.; Sato, F. Tetrahedron Lett. 1995, 36, 6079.
13. (c) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291.
14. (d) Epstein, O. L.; Savchenko, A. I.; Kulinkovich, O. G. Tetrahedron Lett. 1999, 40, 5935.
15. Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
16. (a) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
17. (b) Chaplinski, V.; Winsel, H.; Kordes, M.; de Meijere, A. Synlett 1997, 111.
18. (c) Williams, C. M.; de Meijere, A. J. Chem. Soc., Perkin Trans. 1 1998, 3699.
19. (d) de Meijere, A.; Chaplinski, V.; Gerson, F.; Merstetter, P.; Haselbach, E. J. Org. Chem. 1999, 64, 6951.
20. de Meijere, A.; Williams, C. M.; Kourdioukov, A.; Sviridov, S. V.; Chaplinski, V.; Kordes, M.; Savchenko, A. I.; Stratmann, C.; Noltemeyer, M. Chem.-Eur. J. 2002, 8, 3789.
21. (a) Bertus, P.; Szymoniak, J. Chem. Commun. 2001, 1792.
22. (b) Bertus, P.; Szymoniak, J. J. Org. Chem. 2002, 67, 3965.
23. (c) Bertus, P.; Szymoniak, J. Synlett 2003, 265.
24. (d) Laroche, C.; Bertus, P.; Szymoniak J. Tetrahedron Lett. 2003, 44, 2485.
25. Gandon, V.; Szymoniak, J. Chem. Commun. 2002, 1308.
26. (a) Casey, C. P.; Smith, L. J. Organometallics 1989, 8, 2288.
27. (b) Casey, C. P.; Vosejpka, L. J. S. Organometallics 1992, 11, 738.
28. (a) Brookhart, M.; Liu, Y. Organometallics 1989, 8, 1569.
29. (b) Brookhart, M.; Liu, Y. J. Am. Chem. Soc. 1991, 113, 939.
30. (a) Davis, D. D.; Chambers, R. L.; Johnson, H. T. J. Organomet. Chem. 1970, 25, C13.
31. (b) Davis, D. D.; Black, R. H. J. Organomet. Chem. 1974, 82, C30.
32. (c) Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576.
33. (d) Fleming, I.; Urch, C. J. Tetrahedron Lett. 1983, 24, 4591.
34. (e) Fleming, I.; Urch, C. J. J. Organomet. Chem. 1985, 285, 173.
35. Hydrozirconation of olefins has been shown to proceed by cis addition. (a) Labinger, J. A.; Hart, D. W.; Seibert, W. E., III; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 3851.
36. (b) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
37. 1H NMR spectrum of the alkylzirconium species 2a and 2b, only resonances for the major isomer were readily discernible. The configuration of the major isomer could not be assigned.
38. The reaction of the mixture of 2a and 2b with TMSOTf as the Lewis acid gave a 29% yield of a 5:1 mixture of labeled phenylcyclopropanes 3a:3b.
39. 13
40. In cyclopropanes, cis couplings are larger than trans couplings. Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds; Springer: New York, 2000.
41. Because of deuterium coupling, it was not possible to use line shape simulations to estimate the amount of 4.
42. The regiochemistry of insertion of styrene is shown as having the Ph α to Ti. If the titanacycle had formed with the alternative regiochemistry with Ph β to titanium, the observed stereochemistry of the cyclopropane would also have required retention of configuration at the carbon bonded to titanium.
43. (a) Morlender-Vais, N.; Solodovnikova, N.; Marek, I. Chem. Commun. 2000, 1849.
44. (b) Lee, J.; Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 8127.
45. Wu, Y.-D.; Yu, Z.-X. J. Am. Chem. Soc. 2001, 123, 5777.
46. Fagan, M. A. Ph.D. Thesis, University of Wisconsin-Madison, 1999; p 166.
47. (a) Jensen, F. R.; Nakamaye, K. L. J. Am. Chem. Soc. 1966, 88, 3437.
48. (b) Hoffmann, R. W.; Hölzer, B. Chem. Commun. 2001, 491.
49. 7
50. Ouhamou, N.; Six, Y. Org. Biomol. Chem. 2003, 1, 3007.
51. 13
52. (a) Grant, B.; Djerassi, C. J. Org. Chem. 1974, 39, 968.
53. (b) Kang, M. J.; Jang, J.-S.; Lee, S.-G. Tetrahedron Lett. 1995, 36, 8829.
54. DePuy, C. H.; Breitbeil, F. W.; DeBruin, K. R. J. Am. Chem. Soc. 1966, 88, 3347.