Titanocene(III)-promoted Barbier-type crotylation of carbonyl compounds

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 732-735

  Sancho Sanz, Iris ^a   Miguel, Delia ^a   Millán, Alba ^a   Estévez, Rosa E ^a   Oller López, Juan L ^a   Alvarez Manzaneda, Enrique ^a   Robles, Rafael ^a   Cuerva, Juan M ^a   Justicia, José ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL COMPOUNDS; HIGH YIELD; OPTIMIZED CONDITIONS; SELECTIVE GENERATION; STEREOSELECTIVE METHOD; TITANOCENES;

ALDEHYDES; KETONES; STEREOSELECTIVITY;

CARBONYLATION;

ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; TITANOCENE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROTYLATION; STEREOCHEMISTRY; STEREOISOMERISM; STOICHIOMETRY;

EID: 78651480333     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102269d     Document Type: Article

References (71)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; p 1210.
2. For a list of metals capable of promoting Barbier-type allylations, see: Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 1126 -1133.
3. Barbier, P. Compt. Rend. 1899, 128, 110-111
4. Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181
5. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1997, 118, 12349-12357
6. Inoue, M.; Suzuki, T.; Nakada, M. J. Am. Chem. Soc. 2003, 125, 1140-1141
7. Lee, J.-Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837-1839
8. Cr(II) with syn selectivity: Bandani, M.; Cozzi, P. G.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2000, 39, 2327-2329
9. For relevant reviews, see: Fürstner, A. Chem. Rev. 1999, 99, 991-1045
10. Hargaden, G. C.; Guiry, P. J. Adv. Synth. Catal. 2007, 349, 2407-2424
11. Sm(II) usually gives mixtures of α-and γ-regioisomers: Collin, J.; Bied, C.; Kagan, H. B. Tetrahedron Lett. 1991, 32, 629-630
12. Hamman-Gaudinet, B.; Namy, J.-L.; Kagan, H. B. Tetrahedron Lett. 1997, 38, 6585-6588
13. Di Scala, A.; Garbacia, S.; Hélion, F.; Lannon, M.-I.; Namy, J.-L. Eur. J. Org. Chem. 2002, 2989-2995
14. 2Sm yields preferably anti diastereoisomers: Takaki, K.; Kusudo, T.; Uebori, S.; Nishiyama, T.; Kamata, T.; Yokoyama, M.; Takehira, K.; Mokioka, Y.; Fujiwara, Y. J. Org. Chem. 1998, 63, 4299-4304
15. Basu, M. K.; Banik, B. K. Tetrahedron Lett. 2001, 42, 187-189
16. Hiyama, T.; Obayashi, M.; Nakamura, A. Organometallics 1982, 1, 1249-1251
17. Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049-7052
18. Pétrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910-912
19. Maton, D.; Stivanello, D.; Tagliavini, G. J. Org. Chem. 1996, 61, 2731-2737
20. Zha, Z.; Xie, Z.; Zhou, C.; Chang, M.; Wang, Z. New. J. Chem. 2003, 27, 1297-1300
21. Sain, B.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1992, 33, 4795-4797
22. Nakami, J.; Otera, J.; Suzio, T.; Okawara, R. Organometallics 1983, 2, 191-193
23. Zha, Z.; Quiao, S.; Jiang, J.; Wang, Y.; Miao, Q.; Wang, Z. Tetrahedron 2005, 61, 2521-2527
24. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831-1835
25. Li, X.-R.; Loh, T.-P. Tetrahedron: Asymmetry 1996, 7, 1535-1538
26. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986-997
27. Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849-12859
28. Gansäuer, A.; Lauterbach, T.; Bluhm, H.; Noltenmeyer, M. Angew. Chem., Int. Ed. 1999, 38, 2909-2910
29. Gansäuer, A.; Rosales, A.; Justicia, J. Synlett 2006, 927-929
30. Gansäuer, A.; Justicia, J.; Rosales, A.; Worgull, D.; Rinker, B.; Cuerva, J. M.; Oltra, J. E. Eur. J. Org. Chem. 2006, 4115-4127
31. Gansäuer, A.; Barchuk, A.; Keller, F.; Schmitt, M.; Grimme, S.; Gerenkamp, M.; Mück-Lichtenfeld, C.; Daasbjerg, K.; Svith, H. J. Am. Chem. Soc. 2007, 129, 1359-1371
32. Gansäuer, A.; Fan, C.-A.; Keller, F.; Keil, J. J. Am. Chem. Soc. 2007, 129, 3484-3485
33. Gansäuer, A.; Fan, C.-A.; Piestert, F. J. Am. Chem. Soc. 2008, 130, 6916-6917
34. Gansäuer, A.; Fleckhaus, A.; Lafont, M. A.; Okkel, A.; Kotsis, K.; Anoop, A.; Neese, F. J. Am. Chem. Soc. 2009, 131, 16989-16999
35. Gansäuer, A.; Worgull, D.; Knebel, K.; Huth, I.; Schnakenburg, G. Angew. Chem., Int. Ed. 2009, 48, 8882-8885
36. For relevant reviews, see: Gansäuer, A.; Lauterbach, T.; Narayan, S. Angew. Chem., Int. Ed. 2003, 42, 5556-5573
37. Gansäuer, A.; Justicia, J.; Fan, C.-A.; Worgull, D.; Piestert, F. Top. Curr. Chem. 2007, 279, 25-52
38. Justicia, J.; Rosales, A.; Buñuel, E.; Oller-López, J. L.; Valdivia, M.; Haidour, A.; Oltra, J. E.; Barrero, A. F.; Cárdenas, D. J.; Cuerva, J. M. Chem.-Eur. J. 2004, 10, 1778-1788
39. Justicia, J.; Oller-López, J. L.; Campaña, A. G.; Oltra, J. E.; Cuerva, J. M.; Buñuel, E.; Cárdenas, D. J. J. Am. Chem. Soc. 2005, 127, 14911-14921
40. Justicia, J.; Campaña, A. G.; Bazdi, B.; Robles, R.; Cuerva, J. M.; Oltra, J. E. Adv. Synth. Catal. 2008, 350, 571-576
41. Cuerva, J. M.; Campaña, A. G.; Justicia, J.; Rosales, A.; Oller-López, J. L.; Robles, R.; Cárdenas, D. J.; Buñuel, E.; Oltra, J. E. Angew. Chem., Int. Ed. 2006, 45, 5522-5526
42. Campaña, A. G.; Bazdi, B.; Fuentes, N.; Robles, R.; Cuerva, J. M.; Oltra, J. E.; Porcel, S.; Echavarren, A. M. Angew. Chem., Int. Ed. 2008, 47, 7515-7519
43. Paradas, M.; Campaña, A. G.; Jiménez, T.; Robles, R.; Oltra, J. E.; Buñuel, E.; Justicia, J.; Cárdenas, D. J.; Cuerva, J. M. J. Am. Chem. Soc. 2010, 132, 12748-12756
44. For a relevant review, see: Cuerva, J. M.; Justicia, J.; Oller-López, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264, 63-91
45. Rosales, A.; Oller-López, J. L.; Justicia, J.; Gansäuer, A.; Oltra, J. E.; Cuerva, J. M. Chem. Commun. 2004, 2628-2629
46. Estévez, R. E.; Justicia, J.; Bazdi, B.; Fuentes, N.; Paradas, M.; Choquesillo-Lazarte, D.; García-Ruiz, J. M.; Robles, R.; Gansäuer, A.; Cuerva, J. M.; Oltra, J. E. Chem.-Eur. J. 2009, 15, 2774-2791
47. Justicia, J.; Sancho-Sanz, I.; Álvarez-Manzaneda, E.; Oltra, J. E.; Cuerva, J. M. Adv. Synth. Catal. 2009, 351, 2295-2300
48. anti selectivity: Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441-1454
49. Sato, F.; Iida, K.; Iijima, S.; Moriya, H.; Sato, M. J. Chem. Soc., Chem. Commun. 1981, 1140-1141
50. Sato, F.; Uchiyama, H.; Iida, K.; Kobayashi, Y.; Sato, M. J. Chem. Soc., Chem. Commun. 1983, 921-922
51. Collins, S.; Dean, W. P.; Ward, D. G. Organometallics 1988, 7, 2289-2293
52. Collins, S.; Kuntz, B. A.; Hong, Y. J. Org. Chem. 1989, 54, 4154-4158
53. Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881-3882
54. syn selectivity: Reetz, M. T.; Saurwald, M. J. Org. Chem. 1984, 49, 2292-2293
55. Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1691-1694
56. Nowrouzi, F.; Thadani, A. N.; Batey, R. A. Org. Lett. 2009, 11, 2631-2634 and references cited therein
57. Itoh, J.; Han, S. B.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 6313-6316 and references cited therein
58. Moreover, it is known that the nature of the halide coordinated to titanocene(III) also affects the syn: anti stereoselection; see ref 14b.
59. Gansäuer, A. Chem. Commun. 1997, 457-458
60. Paradas, M.; Campaña, A. G.; Estévez, R. E.; Álvarez de Cienfuegos, L.; Jiménez, T.; Robles, R.; Cuerva, J. M.; Oltra, J. E. J. Org. Chem. 2009, 74, 3616-3619
61. Jana, S.; Guin, C.; Roy, S. C. Tetrahedron Lett. 2004, 45, 6575-6577
62. For recent overviews on organometallic catalysts, see: Shibasaki, M.; Yamamoto, Y., Eds. Multimetallic Catalysts in Organic Synthesis; Wiley VCH: Weinheim, Germany, 2004.
63. Roberts, S. M.; Xiao, J.; Whittall, J.; Pickett, T. E., Eds. Catalysts for Fine Chemical Synthesis. Metal Catalysed Carbon-Carbon Bond-Forming Reactions; Wiley: New York, 2004; Vol. 3.
64. The excess of Mn and 2,4,6-collidine can be recovered at the end of the experiments by filtering and simple acid-base extraction. Subsequently, both recovered collidine and Mn dust can be used in further experiments.
65. Sato, F.; Iijima, S.; Sato, M. Tetrahedron Lett. 1981, 22, 243-246
66. The existence of crotyl radicals as intermediates in this reaction was confirmed by carrying out some experiments with 3-chloro-1-butene as a pronucleophile. The results were identical to those obtained from crotyl chloride.
67. Fernández-Mateos, A.; Herrero Teijón, P.; Mateos Burón, L.; Rabanedo Clemente, R.; Rubio González, R. J. Org. Chem. 2007, 72, 9973-9982
68. It is generally assumed that coupling reactions between free radicals do not require any activation energy because new bonds are formed rather than existing ones broken; see: Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; p 738.
69. 4 cannot completely drive the reaction to the γ-isomer.
70. Enemærke, R. J.; Larsen, J.; Skrydstrup, T.; Daasbjerg, K. J. Am. Chem. Soc. 2004, 126, 7853-7864
71. All new compounds are fully described in the Supporting Information.