Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents

Journal of the American Chemical Society

Volumn 133, Issue 23, 2011, Pages 9119-9123

  Lauer, Andrew M ^a   Mahmud, Farzeen ^a   Wu, Jimmy ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE AREA; ALLYLIC ALKYLATION; ALLYLIC ALKYLATION REACTIONS; ALLYLIC HALIDES; ALLYLIC SUBSTITUTION; GENERAL METHOD; GRIGNARD REAGENT; ORGANOMAGNESIUM; PHOSPHOROTHIOATE ESTERS; PHOSPHOROTHIOATES; REGIOCONTROL; SIMPLE PROTOCOL;

CATALYSIS; ESTERIFICATION; ESTERS; SODIUM; SUBSTITUTION REACTIONS;

ALKYLATION;

COPPER; ELECTROPHILE; GRIGNARD REAGENT; HALIDE; PHOSPHOROTHIOIC ACID DERIVATIVE; REAGENT;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; PROCESS OPTIMIZATION;

EID: 79958838332     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202954b     Document Type: Article

References (61)

1. N2′. In Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; CRC Press: New York, 1996; pp 455-496.
2. Jackowski, O.; Alexakis, A. Angew. Chem., Int. Ed. 2010, 49, 3346
3. Fujisawa, T.; Iida, S.; Yukizaki, H.; Sato, T. Tetrahedron Lett. 1983, 24, 5745
4. Kar, A.; Argade, N. P. Synthesis 2005, 2995
5. Breit, B.; Derrel, P. Copper-mediated Diastereoselecitve Conjugate Addition and Allylic Substitution Reactions. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VGH: Weinheim, 2002, pp 210-223.
6. Knochel, P.; Gavryushin, A.; Brade, K. Functionalized Organomagnesium Compounds: Synthesis and Reactivity In The Chemistry of Organomagnesium Compounds; Rappoport, Z.; Marek, I., Eds.; The Chemistry of Functional Groups; John Wiley & Sons: Chichester, 2008; Part 2, pp 557-558.
7. Falciola, C. A.; Alexakis, A. Eur. J. Org. Chem. 2008, 3765
8. Bäckvall, J.-E.; Sellén, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615
9. Bäckvall, J.-E.; Persson, E. S. M.; Bombrun, A. J. Org. Chem. 1994, 59, 4126
10. Julia, M.; Righini, A.; Verpeaux, J.-N. Tetrahedron Lett. 1979, 20, 2393
11. Barsanti, P.; Calò; Lopez, L.; Marchese, G.; Naso, F.; Pesce, G. J. Chem. Soc., Chem. Commun. 1978, 1085
12. Takabe, K.; Uchiyama, Y.; Okisaka, K.; Yamada, T.; Katagiri, T.; Okazaki, T.; Oketa, Y.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1985, 42, 5153
13. Norinder, J.; Bogár, K.; Kanupp, L.; Bäckvall, J.-E. Org. Lett. 2007, 9, 5095
14. Takashima, Y.; Kobayashi, Y. J. Org. Chem. 2009, 74, 5920
15. Tseng, C. C.; Paisley, S. D.; Goering, H. L. J. Org. Chem. 1986, 51, 2884
16. Tseng, C. C.; Yen, S.-J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892
17. Underiner, T. L.; Paisley, S. D.; Schmitter, J.; Lesheski, L.; Goering, H. L. J. Org. Chem. 1989, 54, 2369
18. Gendreau, Y.; Normant, J. F. Tetrahedron Lett. 1979, 35, 1517
19. Hudlicky, T.; Tian, X.; Königsberger, K.; Rouden, J. J. Org. Chem. 1994, 59, 4037
20. Yanagisawa, A.; Hibino, H.; Nomura, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 5879
21. Araki, S.; Sato, T.; Butsugan, Y. J. Chem. Soc., Chem. Commun. 1982, 285
22. Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 203
23. Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; Bäckvall, J. E.; van Koten, G. Chem.-Eur. J. 1995, 1, 351
24. Dieter, R. K.; Gore, V. K.; Chen, N. Org. Lett. 2004, 6, 763
25. Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 1365
26. Carrillo-Marquez, T.; Caggiano, L.; Jackson, R. F. W.; Grabowska, U.; Rae, A.; Tozer, M. J. Org. Biolmol. Chem. 2005, 3, 4117
27. Fürstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773
28. Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017
29. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130
30. Yanagisawa, A.; Hibino, H.; Nomura, N.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 5879
31. Araki, S.; Sato, T.; Butsugan, Y. J. Chem. Soc., Chem. Commun. 1982, 285
32. Djahanbini, D.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 203
33. Han, X.; Zhang, Y.; Wu, J. J. Am. Chem. Soc. 2010, 132, 4104
34. We have also demonstrated that phosphorothioate esters can be used in the one-step synthesis of thioethers from alcohols, see: Robertson, F.; Wu, J. Org. Lett. 2010, 12, 2668
35. Han, X.; Wu, J. Org. Lett. 2010, 12, 5780
36. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422
37. Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Fournioux, X. Synlett 2001, 927
38. Trost, B. M.; Klun, T. P. J. Org. Chem. 1980, 45, 425
39. Lee, Y.; Akiyama, K.; Gillingham, D. G.; Brown, M. K.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 446
40. Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317
41. Kabalka, G. W.; Al-Masum, M. Org. Lett. 2006, 8, 11
42. Durand, S.; Parrain, J.-L.; Santelli, M. J. Chem. Soc., Perkin Trans. 1 2000, 253
43. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063
44. Persson, E. S. M.; van Klaveren, M.; Grove, D. M.; Bäckvall, J.-E.; van Koten, G. Chem.-Eur. J. 1995, 1, 351
45. Karlström, A. S. E.; Bäckvall, J.-E. Chem.-Eur. J. 2001, 7, 1981
46. Dorigo, A. E.; Wanner, J.; von Ragué Schleyer, P. Angew. Chem., Int. Ed. Engl. 1995, 34, 476
47. Mori, S.; Nakamura, E. Mechanisms of Copper-Mediated Addition and Substitution Reactions. In Modern Organocopper Chemistry. Krause, N., Ed.; Wiley-VGH: Weinheim, 2002, p 329.
48. For references regarding influences on the rate of reductive elimination, see: Yoshikai, N.; Zhang, S.-L.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 12862
49. Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287
50. Marino, J. P.; Floyd, D. M. Tetrahedron Lett. 1979, 20, 675
51. Levisalles, J.; Rudler-Chauvin, M.; Rudler, H. J. Organomet. Chem. 1977, 136, 103
52. Goliaszewski, A.; Schwartz, J. J. Am. Chem. Soc. 1984, 106, 5028
53. Levisalles, J.; Rudler-Chauvin, M.; Rudler, H. J. Organomet. Chem. 1977, 136, 103
54. For other studies utilizing isotopically-labeled, unbiased substrates, see ref 3h and Goering, H. L.; Singleton, V. D., Jr. J. Am. Chem. Soc. 1976, 98, 7854
55. Yamamoto, Y.; Yamamoto, S.; Yatagai, H.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 2318
56. Julia, M.; Righini-Tapif, A.; Verpeaux, J.-N. Tetrahedron 1983, 39, 3283
57. Julia, M.; Righini, A.; Verpeaux, J.-N. Tetrahedron Lett. 1979, 20, 2393
58. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130
59. Goering, H. L.; Tseng, C. C. J. Org. Chem. 1983, 48, 3986
60. Goering, H. L.; Seitz, E. P., Jr.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304
61. Enantiomeric excess was determined on the corresponding carboxylic acid after ozonolysis followed by oxidation with the Jones reagent. For reference, see: Perrone, S.; Knochel, P. Org. Lett. 2007, 9, 1041