Directed carbozincation reactions of cyclopropene derivatives

Journal of the American Chemical Society

Volumn 131, Issue 15, 2009, Pages 5382-5383

  Tarwade, Vinod ^a   Liu, Xiaozhong ^a   Yan, Ni ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOMETALATION; CARBOXYLATE ESTERS; CARBOXYLIC ESTERS; CYCLOPROPENE DERIVATIVES; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; DIORGANOZINC REAGENTS; ELECTROPHILES; FACIAL SELECTIVITY; GRIGNARD REAGENT; IN-SITU; ORGANOZINC REAGENTS; OXAZOLIDINONE; STEREOSPECIFIC REACTION; TRANSITION-METAL-CATALYZED REACTIONS;

ACETYLENE; CARBOXYLATION; ESTERIFICATION; ORGANOMETALLICS; PROPYLENE; STEREOSELECTIVITY; TRANSITION METALS;

ESTERS;

ALKENE DERIVATIVE; CARBONYL DERIVATIVE; COPPER COMPLEX; CYCLOPROPANE DERIVATIVE; PROPYLENE; CYCLOPROPENE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ORGANOMETALLIC COMPOUND; ZINC;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; HYDROBORATION; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY;

CYCLOPROPANES; INDICATORS AND REAGENTS; ORGANIC CHEMISTRY PROCESSES; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 67849133453     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja900949n     Document Type: Article

References (51)

1. For a review of facially selective cyclopropene carbometalation reactions, see: (a) Fox, J. M.; Yan, N. Curr. Org. Chem. 2005, 9, 719.
2. For recent examples, seeref 3 and: (b) Yin, J.; Chisholm, J. D. Chem. Commun. 2006, 632.
3. (c) Hirashita, T.; Shiraki, F.; Onishi, K.; Ogura, M.; Araki, S. Org. Biomol. Chem. 2007, 5, 2154, and references therein.
4. Recent reviews of cyclopropene chemistry: (a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
5. (b) Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221.
6. (c) Marek, I.; Simaan, S.; Masarwa, A. Angew. Chem., Int. Ed. 2007, 46, 7364.
7. (d) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295.
8. Stereoselective carbomagnesiation reactions of cyclopropenes: (a) Simaan, S.; Masariva, A.; Bertus, P.; Marek, I. Angew. Chem., Int. Ed. 2006, 45, 3963.
9. (b) Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569.
10. (c) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 978.
11. (d) Liao, L.-a.; Fox, J. M. J. Am. Chem. Soc. 2002, 124, 14322.
12. (e) Yang, Z.; Xie, X. C.; Fox, J. M. Angew. Chem., Int. Ed. 2006, 45, 3960.
13. (f) Liu, X. Z.; Fox, J. M. J. Am. Chem. Soc. 2006, 128, 5600.
14. (g) Richey, H. G., Jr.; Bension, R. M. J. Org. Chem. 1980, 45, 5036.
15. Selected references to catalytic cyclopropenation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796.
16. (b) Baird, M. S. In Carbocyclic Three-Membered Ring Compounds, 4th ed.; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1996; Vol. E17d, pp 2695-2744.
17. (c) Petiniot, N.; Anciaux, A. J.; Noels, A. F.; Hubert, A. J.; Teyssie, P. Tetrahedron Lett. 1978, 19, 1239.
18. (d) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
19. (e) Díaz-Requejo, M. M.; Mairena, M. A.; Belderrain, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. Chem. Commun. 2001, 1804.
20. Enantioselective procedures: (f) Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916.
21. (g) Lou, Y.; Remarchuk, T. P.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 14223.
22. (h) Weatherhead-Kloster, R. A.; Corey, E. J. Org. Lett. 2006, 8, 171.
23. (i) Doyle, M. P.; Protopopova, M.; Muller, P.; Ene, D.; Shapiro, E. A. J. Am. Chem. Soc. 1994, 116, 8492.
24. (j) Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233.
25. (a) Davies, H. M. L.; Walji, A. M. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 301-340.
26. (b) Davies, H. M. L.; Bechwith, R. Chem. Rev. 2003, 103, 2861.
27. (c) Doyle, M. P. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 341-356.
28. (d) Thompson, J. L.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 6090.
29. (e) Panne, P.; DeAngelis, A.; Fox, J. M. Org. Lett. 2008, 10, 2987.
30. Alexakis, A.; Bäckvall, J. E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796.
31. (a) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198.
32. (b) Nalesnik, T. E.; Freudenberger, J. H.; Orchin, M. J. Organomet. Chem. 1982, 236, 95.
33. (c) Matsui, Y.; Orchin, M. J. Organomet. Chem. 1983, 244, 369.
34. For hydroformylations controlled by steric effects, see: (d) Sherrill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804.
35. For hydrometalation reactions controlled by steric effects, see: (e) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566.
36. (f) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688.
37. (g) Trofimov, A.; Rubina, M.; Rubin, M.; Gevorgyan, V. J. Org. Chem. 2007, 72, 8910.
38. (h) Alnasleh, B. K.; Sherrill, W. M.; Rubin, M. Org. Lett. 2008, 10, 3231.
39. Recent examples of hydroxyl-directed hydrometalation reactions: (i) Zohar, E.; Marek, I. Org. Lett. 2004, 6, 341.
40. (j) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
41. Stoll, A. T.; Negishi, E-i. Tetrahedron Lett. 1985, 26, 5671.
42. (a) Kubota, K.; Isaka, M.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 5867.
43. (b) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179.
44. (c) Kubota, K.; Mori, S.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 13334.
45. (d) Nakamura, M.; Inoue, T.; Sato, A.; Nakamura, E. Org. Lett. 2000, 2, 2193.
46. Nucleophilic addition reactions of zincated amides, esters, and hydrazones: (e) Nakamura, E.; Kubota, K. J. Org. Chem. 1997, 62, 792.
47. Smith, M. A.; Richey, H. G., Jr. Organometallics 2007, 26, 609.
48. The sense of the regioselectivity is precedented (see ref 1a).
49. 2Zn and 2a; only 3a was obtained in these reactions.
50. Seebach, D.; Behrendt, L.; Felix, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008.
51. Yan, N.; Liu, X.; Pallerla, M. K. J. Org. Chem. 2008, 73, 4283.