Stereodivergent catalytic doubly diastereoselective nitroaldol reactions using heterobimetallic complexes

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2231-2234

  Sohtome, Yoshihiro ^a   Kato, Yuko ^a   Handa, Shinya ^a   Aoyama, Naohiro ^a   Nagawa, Keita ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; LANTHANUM; LITHIUM; NITROGEN; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; LANTHANUM; LITHIUM; NITROGEN; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 52649127408     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800653d     Document Type: Article

References (55)

1. Recent reviews: (a) Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
2. (b) Chapman, C. J.; Frost, C. G. Synthesis 2007, 1.
3. (c) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
4. (d) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
5. (e) Kolodiazhnyi, O. I. Tetrahedron 2003, 59, 5953.
6. A review: Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
7. Reviews: (a) Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561.
8. (b) Boruwa, J.; Gogoi, N.; Saikia, P. P.; Barua, N. C. Tetrahedron: Asymmetry 2006, 17, 3315.
9. (c) Palomo, C.; Oiarbide, M.; Mielgo, A. Angew. Chem., Int. Ed. 2004, 43, 5442.
10. (d) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
11. Selected early works on catalytic asymmetric nitroaldol reactions: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418.
12. (b) Sasai, H.; Kim, W.-S.; Suzuki, T.; Shibasaki, M.; Mitsuda, M.; Hasegawa, J.; Ohashi, T. Tetrahderon Lett. 1994, 35, 6123.
13. (c) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
14. For other works see a review: (d) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. 1997, 36, 1236.
15. For related recent works in our group, see: (a) Tosaki, S.; Hara, K.; Gnanadesikan, V.; Morimoto, H.; Harada, S.; Sugita, M.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 11776.
16. (b) Mihara, H.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2008, 3, 359.
17. (c) Nitabaru, T.; Kumagai, N.; Shibasaki, M. Tetrahedron Lett. 2008, 49, 272.
18. For selected works by other groups, see: (a) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Int. Ed. 1999, 38, 1931.
19. (b) Christensen, C.; Juhl, K; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 4875. and references therein.
20. (c) Trost, B. M.; Yeh, V. S. C. Angew. Chem., Int. Ed. 2002, 41, 861.
21. (d) Ooi, T.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 2054.
22. (e) Evans, D. A.; Seidel, D.; Rueping, M.; Lam, H. W.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2003, 125, 12692.
23. (f) Palomo, C.; Oiarbide, M.; Laso, A. Angew. Chem., Int. Ed. 2005, 44, 3881.
24. (g) Sohtome, Y.; Takemura, N.; Takada, K.; Takagi, R.; Iguchi, T.; Nagasawa, K. Chem. Asian J. 2007, 2, 1150. and references therein.
25. (h) Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732.
26. (i) Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929.
27. (j) Arai, T.; Watanabe, M.; Yanagisawa, A. Org. Lett. 2007, 9, 3595. and references therein.
28. (k) Uraguchi, D.; Sakaki, S.; Ooi, T. J. Am. Chem. Soc. 2007, 129, 12392.
29. (l) Xiong, Y.; Wang, F.; Huang, X.; Wen, Y.; Feng, X. Chem. Eur. J. 2007, 13, 829.
30. (m) Bandini, M.; Benaglia, M.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. Org. Lett. 2007, 9, 2151.
31. (n) Tur, F.; Saá, J. M. Org. Lett. 2007, 9, 5079. For other examples, see reviews in ref 3.
32. (a) Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261.
33. (b) Hanessian, S.; Devasthale, P. V. Tetrahedron Lett. 1996, 37, 987.
34. (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. 1990, 29, 1169.
35. (d) Fernández, R.; Gasch, C.; Gómez-Sánchez, A.; Vílchez, J. E.; Castro, A. L.; Diánez, M. J.; Estrada, M. D.; Pérez-Garrido, S. Carbohydr. Res. 1993, 247, 239.
36. (e) Soengas, R. G.; Estévez, J. C.; Estévez, R. J. Tetrahedron: Asymmetry 2003, 14, 3955.
37. (f) Bernardi, L.; Bonini, B. F.; Dessole, G.; Fochi, M.; Comes-Franchini, M.; Gavioli, S.; Ricci, A.; Varchi, G. J. Org. Chem. 2003, 68, 1418.
38. Hanessian et al. reported an exceptional example using (R)-LLB 1 as a chiral catalyst. Although there remained a room for improvement in diastereoselectivity (anti-syn-5:syn-syn-6:others = 20:5.5:2.5), anti-syn-5 was obtained as a major product. See Hanessian, S.; Brassard, M. Tetrahedron 2004, 60, 7621.
39. (a) Reviews on Lewis acid-Brønsted base bifunctional catalysis Matsunaga, S.; Shibasaki, M. Bull. Chem. Soc. Jpn. 2008, 81, 60.
40. (b) Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269.
41. (c) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
42. (a) Handa, S.; Nagawa, K.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2008, 47, 3230.
43. For related bimetallic Schiff base catalysts, see: (b) Handa, S.; Gnanadesikan, V.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 4900.
44. (c) Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170.
45. For the synthesis of aldehyde 3 without racemization: Tokuyama, H.; Yokoshima, S.; Lin, S.-C.; Li, L.; Fukuyama, T. Synthesis 2002, 1121, and references therein.
46. Synthesis of nitroalkane 4a: Jäger, V.; Poggendorf, P. Org. Synth. 1997, 74, 130. For the use of nitroacetaldehyde diethyl acetal for anti-anti-selective nitroaldol reaction, see ref 7c.
47. The stereochemistry of 5aa was determined by O-methyl mandelate method: (a) Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4202.
48. (b) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370. See the Supporting Information.
49. The stereochemistry of 6aa was unequivocally determined by X-ray crystallographic analysis. See the Supporting Information.
50. Trials to synthesize anti,syn-5 by mismatched (R,R)-Pd-La complex 2 failed. (R,R)-Pd-La complex 2 afforded products 6aa as a major adduct in lower dr and yield (6aa:others = 8:1, 61% yield) than (S,S)-Pd-La complex 2.
51. LLB 1 is known as a suitable catalyst for syn-selective nitroaldol reaction of prochiral aldehydes with nitroehthane and nitroethanol (ref 4c). The Pd-La-Schiff base complex 2 gave anti-nitroaldol adducts in the reaction of prochiral aldehydes with nitroehthane (ref 10a). Although the precise reason why the Pd-La complex 2 gave syn,syn-6 with nitroalkane 4a has not been clarified yet, we speculate that coordinating dimethylacetal moiety in nitroalkane 4a may be important for changing the geometry of nitronate generated from 4a. Further mechanistic studies are required for more detailed discussion.
52. For related reports utilizing intramolecular hydrogen bonding for anti-Felkin-Anh stereocontrol of N-Boc-protected R-amino aldehydes, see: (a) Jung, C.-K.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 17051.
53. (b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439.
54. (c) Dondoni, A.; Perrone, D.; Merino, P. J. Org. Chem. 1995, 60, 8074.
55. Aldehyde 3g lacking an N-H group gave much less satisfactory results with the Pd-La Schiff base complex 2.