Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to nitroalkenes

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7494-7497

  McCooey, Séamus H ^a   McCabe, Thomas ^a   Connon, Stephen J ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; NITROGEN COMPOUNDS; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DIMETHYL CHLOROMALONATE; NITROCYCLOPROPANES; ORGANOCATALYTIC METHODOLOGY; STEREOSELECTIVE SYNTHESIS;

PARAFFINS;

CYCLOPROPANE DERIVATIVE; NITRO DERIVATIVE; NITROALKANE;

ADDITION REACTION; ARTICLE; CATALYSIS; CONJUGATION; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; CATALYSIS; CYCLIZATION; CYCLOPROPANES; MOLECULAR STRUCTURE; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 33749008198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0613838     Document Type: Article

References (66)

1. (a) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625.
2. (b) Donaldson, W. A. Tetrahedron 2001, 57, 8589.
3. (c) Faust, D. Angew. Chem., Int. Ed. 2001, 40, 2251.
4. (a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
5. (b) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-H.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
6. (a) Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229.
7. (b) Davies, H. M. L. Tetrahedron 1993, 49, 5203.
8. For reviews on the synthesis and applications of cyclopropyl derivatives of β-amino acids see: (a) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
9. (b) Cativelia, C.; Diaz-de-Viellgas, M. D. Tetrahedron: Asymmetry 2000, 11, 645.
10. Recent application: De Pol, S.; Zorn, C.; Klein, C. D.; Zerbe, O.; Reiser, O. Angew. Chem., Int. Ed. 2004, 43, 511.
11. Reviews: (a) Lebel, H.; Marcoux, F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
12. (b) Hartley, R. C.; Caldwell, S. T. J. Chem. Soc., Perkin Trans. 1 2000, 477.
13. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
14. Aggarwal, V. K.; Smith, H. W.; Jones, R. V. H.; Fieldhouse, R. Chem. Commun. 1997, 1785.
15. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int Ed. 2001, 40, 1433.
16. (a) Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2003, 42, 828.
17. (b) Bremeyer, N.; Smith, S. C.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 2681.
18. (c) Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641.
19. Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
20. For the first reports of a ylide-mediated cyclopropanation see: Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
21. For representative recent developments in catalytic asymmetric ylide-based cyclopropanation see: (a) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 124, 2432.
22. (b) Aggarwal, V. K. Acc. Chem. Res. 2004, 37, 611.
23. Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168.
24. (a) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
25. (b) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
26. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
27. Charette recently reported the efficient Cu-catalyzed asymmetric synthesis of 1-nitro-cyclopropylcarboxylates from electron-rich olefins: Moreau, B.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 18014.
28. Barrett, A. G. M.; Grabowski, G. C. Chem. Rev. 1986, 86, 751.
29. For reviews of asymmetric addition reactions to nitroalkenes see: (a) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
30. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
31. (c) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
32. Aggarwal has reported the cycloaddition of sulfonium ylides to Michael acceptors which gives good yields/stereoselectivity with enone substrates but poor yields and diastereoselectivities with nitroolefins. Aggarwal, V. K.; Smith, H. W.; Hynd, G.; Jones, R. V. H.; Fieldhouse, R.; Spey, S. E. J. Chem. Soc., Perkin Trans. 1 2000, 3267.
33. (a) Asunskis, J.; Shechter, H. J. Org. Chem. 1968, 33, 1164.
34. (b) Zindel, J.; de Meijere, A. J. Org. Chem. 1995, 60, 2968.
35. (c) Galley, G.; Hübner, J.; Anklam, S.; Jones, P. G.; Pätzel, M. Tetrahedron Lett. 1996, 37, 6307.
36. (d) Hübner, J.; Liebscher, J.; Pätzel, M. Tetrahedron 2002, 58, 10485.
37. (e) Parham, W. E.; Braxton, H. G.; Serres, C. J. Org. Chem. 1961, 26, 1831.
38. For alternative preparations of nitrocyclopropanes from nonnitroolefin sources see: (a) Wurz, R. P.; Charette, A. B. J. Org. Chem. 2004, 69, 1262.
39. (a) O'Bannon, P. E.; Dailey, W. P. J. Org. Chem. 1990, 55, 353-355.
40. (a) Yu, J.; Falck, J. R. J. Org. Chem. 1992, 57, 3757.
41. (b) O'Bannon, P. E.; Dailey, W. P. Tetrahedron 1990, 46, 7341.
42. (c) Kai, Y.; Knochel, P.; Kwiatkowski, S.; Dunitz, J. D.; Oth, J. F. M.; Seebach, D.; Kalinowski, H.-O. Helv. Chim. Acta 1982, 65, 137.
43. (d) Kohler, E. P.; Darling, S. F. J. Am. Chem. Soc. 1930, 52, 1174.
44. (a) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367.
45. (b) Murtagh, J. E.; McCooey, S. H.; Connon, S. J. Chem. Commun. 2005, 227.
46. (c) Faltin, C.; Fleming, E. M.; Connon, S. J. J. Org. Chem. 2004, 69, 6496.
47. Zlatopolskiy, B. D.; Loscha, K.; Alvermann, P.; Kozhushkov, S. I.; Nikolaev, S. V.; Zeeck, A.; de Meijere, A. Chem.-Eur. J. 2004, 10, 4708.
48. For alternative systems for the same reaction see: (a) Li, H.; Wang, Y.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2004, 126, 9906.
49. (b) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
50. (c) Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun. 2005, 4481.
51. Recent reviews of hydrogen bond-faciltated organocatalysis: (a) Connon, S. J. Chem.-Eur. J. 2006, 12, 5418.
52. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
53. (c) Takemoto, Y. Org. Biomol. Chem. 2005, 3, 4299.
54. (d) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
55. 3) are (a) triethylamine = 10.9: Kuna S.; Pawlak, Z.; Tusk, M. J. Chem. Soc., Faraday Trans. 1982, 78, 2685.
56. (b) DMAP = 9.7: Chrystuik, E.; Williams, A. J. Am. Chem. Soc. 1987, 109, 3040.
57. (c) N-ethylmorpholine = 7.7: Hall, H. K., Jr. J. Phys. Chem. 1956, 60, 63.
58. (d) quinuclidine = 11.3: Grob, C. A. Helv. Chim. Acta 1985, 68, 882.
59. N2-type reactions relative to more common polar aprotic solvents (such as MeCN and THF), alternative mechanisms involving DBU-mediated halogen transfer cannot be ruled out at this time. It is interesting to note that DBU is also an excellent base for the Bingel reaction, see: (a) Bingel, C. Chem. Ber. 1993, 126, 1957.
60. (b) Nierengarten, J.-F.; Gramlich, V.; Cardullo, F.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2101.
61. Kohler found that an α-bromoadduct similar to 8 could be cyclized in poor yield (>30%) on reflux in excess methanolic KOAc (see ref 20d). A later report suggested that a p-Me analogue of 4 could be prepared via electroreduction of the chloromalonate in the presence of the Michael acceptor (no yield given): Le Menn, J.-C.; Tallec, A.; Sarrazin, J. Can. J. Chem. 1991, 69, 761.
62. For a useful oxidative cyclization using KF/alumina of the Michael adducts between malonate esters and electron deficient olefins (including nitroolefins): Villemin, D.; Thibault-Starzyk, F.; Hachemi, M. Synth. Commun. 1994, 24, 1425.
63. See Supporting Information for details.
64. The Michael addition reaction promoted by 6 and 7 proceeded to completion in all cases.
65. It is interesting to note that the quinidine derived DHQD furnished the same major product enantiomer as the quinine-derived 6. This is contrary to the trend previously observed in the corresponding catalyzed addition of dimethyl malonate to 2 (see ref 21a).
66. Racemization of the product by DBU has been discounted as the ee of enantioenriched 4 remained unchanged after stirring in THF (1.0 M) in the presence of DBU (1.0 equiv) for 24 h at room temperature.