Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands

Organic Letters

Volumn 5, Issue 5, 2003, Pages 681-684

  Boiteau, Jean Guy ^a   Imbos, Rosalinde ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; LACTONE DERIVATIVE; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE; RHODIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0038251459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027465+     Document Type: Article

References (45)

1. (a) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353 and references therein.
2. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Leggy, A. L. In Modern Organocopper Chemistry; Krause, N., Ed; Wiley-VCH: Weinheim, 2002; Chapter 7, pp 224-255. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
3. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Leggy, A. L. In Modern Organocopper Chemistry; Krause, N., Ed; Wiley-VCH: Weinheim, 2002; Chapter 7, pp 224-255. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
4. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Leggy, A. L. In Modern Organocopper Chemistry; Krause, N., Ed; Wiley-VCH: Weinheim, 2002; Chapter 7, pp 224-255. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
5. For reviews, see: (a) Krause, N.; Gerold, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 186-204. (b) Krause, N. Angew. Chem., Int. Ed. 1998, 37, 283-285. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Leggy, A. L. In Modern Organocopper Chemistry; Krause, N., Ed; Wiley-VCH: Weinheim, 2002; Chapter 7, pp 224-255. (d) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236.
6. (a) Malda, H.; van Zijl, A. W.; Arnold, L. A.; Feringa, B. L. Org. Lett. 2001, 3, 1169-1171.
7. (b) Naasz, R.; Arnold, L. A.; Minnaard, A. J.; Feringa B. L. Angew. Chem., Int. Ed. 2001, 40, 927-930.
8. (c) Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. J. Am. Chem. Soc. 1999, 121, 1104-1105.
9. (d) Imbos, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185.
10. (e) Naasz, R.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Chem. Commun. 2001, 735-736.
11. (f) Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 930-932.
12. See, for examples: (a) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841-5842. (b) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254. (c) Jagt, R. B. C.; Imbos, R.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. Isr. J. Chem. 2001, 41, 221-229.
13. See, for examples: (a) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841-5842. (b) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254. (c) Jagt, R. B. C.; Imbos, R.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. Isr. J. Chem. 2001, 41, 221-229.
14. See, for examples: (a) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841-5842. (b) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Org. Chem. 2002, 67, 7244-7254. (c) Jagt, R. B. C.; Imbos, R.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. Isr. J. Chem. 2001, 41, 221-229.
15. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229-4231.
16. (b) Hayashi, T. Synlett 2001, 879-887.
17. (c) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, M. J. Am. Chem. Soc. 1998, 120, 5579-5581.
18. (d) Hayashi, T.; Senda, T.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 1999, 121, 11591-11592.
19. (e) Takaya, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Hayashi, T. Tetrahedron: Asymmetry 1999, 10, 4047-4056.
20. (f) Sakuma, S.; Sakai, M.; Itooka, R.; Hayashi, T. J. Org. Chem. 2000, 65, 5951-5955.
21. (g) Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852-6856.
22. (h) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717.
23. (i) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052-5058.
24. (a) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
25. (b) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91-97.
26. (c) Hayashi, T.; Ishigedani, M. J. Am. Chem. Soc. 2000, 122, 976-977.
27. Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667-669.
28. Hayashi, T.; Tokunaga, N.; Yoshida, K.; Han, J. W. J. Am. Chem. Soc. 2002, 124, 12102-12103.
29. Ueda, M.; Miyaura, N. J. Organomet. Chem. 2000, 595, 31-35.
30. Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martín-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358-5359.
31. Takaya, H.; Akatugawa, S.; Noyori, R. Org. Synth. 1989, 67, 20-32.
32. Takaya, Y.; Ogasawara, M.; Hayashi, T. Chirality 2000, 12, 469-471.
33. 3-catalyzed addition of arylboronic acids to oxabenzonorbornadienes has been reported very recently: Murakami, M.; Igawa, H. Chem. Commun. 2002, 390-391.
34. Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083-4085.
35. (a) Kuriyama, M.; Tomioka, K. Tetrahedron Lett. 2001, 42, 921-923.
36. (b) Kuriyama, M.; Nagai, K.; Yamada, K.-I.; Miwa, Y.; Taga, T.; Tomioka, K. J. Am. Chem. Soc. 2002, 124, 8932-8939.
37. van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; Van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539-11540.
38. Synthesized according to known procedures, see refs 1 and 20. For L6, L8, and L9, see the Supporting Information.
39. 2 was selectioned as the rhodium source of choice. See the Supporting Information.
40. (a) The use of 2.5 equiv of ligand relative to rhodium was chosen for convenience as it was observed that the reaction proceeds better with a slight excess of phosphoramidite (compared to the 1:2 Rh/L ratio). (b) Replacing water by methanol provides the same conversion and ee although reaction time increases.
41. Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552-14553. See also ref 16.
42. Hu, A. G.; Fu, Y.; Xie, J. H.; Zhou, H.; Wang, L.; Zhou, Q. L. Angew. Chem., Int. Ed. 2002, 41, 2348-2350.
43. At 25°C, 63% conversion (84% ee) was reached in 16 h.
44. 2 are employed to achieve complete conversion, since considerable amounts of benzene are formed; see ref 5c.
45. Hayashi recently reported a similar result using a preformed BINAP hydroxorhodium complex; see ref 5i.