Diastereoselective nickel-catalyzed reductive Aldol cyclizations using diethylzinc as the stoichiometric reductant: Scope and mechanistic insight

Journal of the American Chemical Society

Volumn 130, Issue 23, 2008, Pages 7328-7338

  Joensuu, Pekka M ^a   Murray, Gordon J ^a   Fordyce, Euan A F ^a   Luebbers, Thomas ^b   Hon, Wai Lam ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL;

CYCLIZATIONS; DIASTEREOSELECTIVE; DIETHYL ZINC (DEZN); NI(KTFAA)2; REDUCTANT;

NICKEL ALLOYS;

AMIDE; CARBONYL DERIVATIVE; DEUTERIUM; DIETHYLZINC; ESTER; KETONE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; NICKEL;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY;

ACETATES; ALKENES; AMIDES; CYCLIZATION; ESTERS; KETONES; LACTAMS; LACTONES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 44949127247     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0775624     Document Type: Article

References (71)

1. For recent, representative examples, see: (a) Chaulagain, M. R.; Sormunen, G. J.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 9568-9569.
2. (b) Herath, A.; Thompson, B. B.; Montgomery, J. J. Am. Chem. Soc. 2007, 129, 8712-8713.
3. (c) Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 2248-2249.
4. (d) Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 14030-14031.
5. (e) Samih ElDouhaibi, A.; Lozanov, M.; Montgomery, J. Tetrahedron 2006, 62, 11460-11469.
6. (f) Kimura, M.; Ezoe, A.; Mori, M.; Iwata, K.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559-8568.
7. (g) Moslin, R. M.; Miller, K. M.; Jamison, T. F. Tetrahedron 2006, 62, 7598-7610.
8. (h) Knapp-Reed, B.; Mahandru, G. M.; Montgomery, J. J. Am. Chem. Soc. 2005, 127, 13156-13157.
9. (i) Maezaki, N.; Sawamoto, H.; Ishihara, H.; Tanaka, T. Chem. Commun. 2005, 3992-3994.
10. (J) Miller, K. M.; Jamison, T. F. Org. Lett. 2005, 7, 3077-3080.
11. (k) Luanphaisarnnont, T.; Ndubaku, C. O.; Jamison, T. F. Org. Lett. 2005, 7, 2937-2940.
12. (l) Kimura, M.; Miyachi, A.; Kojima, K.; Tanaka, S.; Tamaru, Y. J. Am. Chem. Soc. 2004, 126, 14360-14361.
13. (m) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941-3944.
14. (n) Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc 2004, 126, 3698-3699.
15. (o) Sato, Y.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 9310-9317.
16. (p) Sato, Y.; Sawaki, R.; Saito, N.; Mori, M. J. Org. Chem. 2002, 67, 656-662.
17. (q) Kimura, M.; Ezoe, A.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. 2001, 40, 3600-3602.
18. (r) Shibata, K.; Kimura, M.; Shimizu, M.; Tamaru, Y. Org. Lett. 2001, 3, 2181-2183.
19. (s) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397-400.
20. (t) Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920.
21. For a review, see: Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908.
22. The Zhou and Tamaru groups have reported isolated examples of both inter- and intramolecular reductive couplings of dienyl esters with aldehydes, where coupling occurred α to the ester carbonyl. However, it is the diene functionalities of these substrates that are essential for reaction to proceed, rather than the α,β-unsaturated ester. See refs 1c, 1f, and 1q.
23. Chrovian, C. C.; Montgomery, J. Org. Lett. 2007, 9, 537-540.
24. For a seminal reference, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809-4812.
25. For an extensive collection of reports of catalytic reductive aldol reactions, see references cited within: (b) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2006, 72, 1063-1072.
26. For relevant reviews, see; (c) Nishiyama, H.; Shiomi, T. Top. Curr. Chem. 2007, 279, 105-137.
27. (d) Jang, H.-Y.; Krische, M. J. Eur. J. Org. Chem. 2004, 3953-3958.
28. (e) Jang, H.-Y.; Krische, M. J. Acc. Chem. Res. 2004, 37, 653-661.
29. (f) Huddleston, R. R.; Krische, M. J. Synlett 2003, 12-21.
30. (g) Chiu, P. Synthesis 2004, 2210-2215.
31. (h) Motherwell, W. B. Pure Appl. Chem. 2002, 74, 135-142.
32. Lam, H. W.; Joensuu, P. M.; Murray, G. J.; Fordyce, E. A. F.; Prieto, O.; Luebbers, T. Org. Lett. 2006, 8, 3729-3732.
33. For infermolecular variants of these reactions, see: Lumby, R. J. R.; Joensuu, P. M.; Lam, H. W. Org. Lett. 2007, 9, 4367-4370.
34. The products 4a, 4b, 4d, 4e, 4g, 4i, 4j, 41, and 4m have been described previously (see ref 6). Product 4h has been described previously: Lam, H. W.; Murray, G. J.; Firth, J. D. Org. Lett. 2005, 7, 5743-5746. The relative stereochemistries of the remaining products in Table 1 were assigned by analogy
35. For examples of alkylative aldol cyclizations (sequential 1,4-conjugate addition-intramolecular aldol reactions), see: (a) Caube, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110-1111.
36. (b) Bocknack, B. M.; Wang, L.-C.; Krische, M. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5421-5424.
37. (c) Agapiou, K.; Cauble, D. F.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4528-4529.
38. Compare with results obtained using copper bisphosphine catalysts in conjunction with siloxane reductants: Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225-4228.
39. The products 21a-21d have been described previously (see ref 10), and the relative stereochemistries of the remaining products in Table 2 were assigned by analogy.
40. Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2005, 127, 247-254.
41. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840-871.
42. (a) Ogoshi, S.; Ikeda, H.; Kurosawa, H. Angew. Chem., Int. Ed. 2007, 46, 4930-4932.
43. (b) Ogoshi, S.; Tonomori, K.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 7077-7086.
44. (c) Ogoshi, S.; Ueta, M.; Arai, T.; Kurosawa, H. J. Am. Chem. Soc. 2005, 127, 12810-12811.
45. (d) Ogoshi, S.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802-11803.
46. (a) Hratchian, H. P.; Chowdhury, S. K.; Gutiérrez-García, V. M.; Amarasinghe, K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636-4646.
47. (b) Amarsinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370-372.
48. A more detailed discussion of the putative conversion of intermediates of general structure 31 into zinc enolates is provided in the discussion of reaction mechanism (see Scheme 12).
49. Zimmerman, H. E.; Traxler, M.; D, J. Am. Chem. Soc. 1957, 79, 1920-1923.
50. 2Zn. See: (a) Chaloner, P. A.; Hitchcock, P. B.; Langadianou, E.; Readney, M. J. Tetrahedron Lett. 1991, 32, 6037-6038.
51. (b) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205-1215.
52. 2Zn-mediated conjugate reductions of α,β-unsaturated amides.
53. (a) Fraser, P.; Woodward, S. Chem. - Eur. J. 2003, 9, 776-783.
54. (b) Blake, A. J.; Shannon, J.; Stephens, J. C.; Woodward, S. Chem. - Eur. J. 2007, 13, 2462-2472.
55. 2Zn also resulted in the formation of 49 in ca. 80% conversion. Montgomery and co-workers have shown that bisenone substrates tethered through their β-carbons undergo nickel-catalyzed reductive cyclizations in the presence of organozincs lacking β-hydrogens. See ref 1t.
56. See the Supporting Information for details.
57. Purification of the product of the reaction depicted in eq 19 by column chromatography gave 56a/56b in a 1:1.5 ratio (relative stereochemistries of major and minor isomers not assigned).
58. Seeman, J. I. Chem. Rev. 1983, 83, 83-134.
59. 1H NMR spectra. See: (a) Pederson, B. F.; Pederson, B. Tetrahedron Lett. 1965, 6, 2995-3001.
60. (b) Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett. 1989, 30, 6177-6180.
61. (c) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955-3975.
62. (a) Johnson, J. R.; Tully, P. S.; MacKenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172-6177.
63. (b) Grisso, B. A.; Johnson, J. R.; MacKenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160-5165.
64. (a) Ogoshi, S.; Yoshida, T.; Nishida, T.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 1944-1950.
65. (b) Ogoshi, S.; Tomiyasu, S.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2002, 124, 11598-11599.
66. For relevant examples involving Ni(0)-catalyzed reactions, see: (a) Hirano, K. Yorimitsu, H. Oshima, K. Org. Lett. 2007, 9, 5031-5033.
67. (b) Hirano, K. Yorimitsu, H. Oshima, K. Org. Lett. 2007, 9, 1541-1544.
68. (c) Seiber, J. D. Liu, S. Morken, J. P. J. Am. Chem. Soc. 2007. 129, 2214-2215.
69. (d) Ikeda, S.-i. Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976. See also ref 2.
70. See for example: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
71. (b) Ogasawara, M.; Takizawa, K.-i.; Hayashi, T. Organometallics 2002, 21, 4853-4861.