Chiral amidophosphane-rhodium(I)-catalyzed asymmetric conjugate arylation of acyclic enones with arylboronic acids

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 9, 2009, Pages 1024-1027

  Chen, Qian ^a   Kuriyama, Masami ^b   Hao, Xinyu ^b   Soeta, Takahiro ^b   Yamamoto, Yasutomo ^b   Yamada, Ken Ichi ^b   Tomioka, Kiyoshi ^b  

^a HARBIN INSTITUTE OF TECHNOLOGY   (China)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

, unsaturated ketone; Arylation; Arylboronic acid; Catalytic asymmetric reaction; Conjugate addition

Indexed keywords

2 CYCLOHEXENONE; AMIDE; AMIDOPHOSPHANE; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; ENONE; KETONE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ARYLATION; ASYMMETRIC CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONJUGATION; ENANTIOSELECTIVITY;

BORONIC ACIDS; CATALYSIS; KETONES; PHOSPHINES; RHODIUM; STEREOISOMERISM;

EID: 70349183765     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.1024     Document Type: Article

References (38)

1. Tomioka K., Synthesis, 1990, 541-549 (1990).
2. Kanai M., Shibasaki M., "Catalytic Asymmetric Synthesis," ed. by Ojima I., VCH, Weinheim, 2000, p. 569.
3. Krause N., Hoffmann-Röder A., Synthesis, 2001, 171-196 (2001).
4. Feringa B. L., Naasz R., Imbos R., Arnold L. A., "Modern Organocopper Chemistry," Chapter 7, ed. by Krause N., Wiley-VCH, Weinheim, 2002.
5. Christoffers J., Koripelly G., Rosiak A., Rössle M., Synthesis, 2007, 1279-1300 (2007).
6. Tomioka K., "Comprehensive Asymmetric Catalysis Supplement to Chapter 31.1," ed. by Jacobsen E. N., Pfaltz A., Yamamoto H., Springer, New York, 2004, pp. 109-124.
7. Alexakis A., Benhaim C., Eur. J. Org. Chem., 2002, 3221-3236 (2002).
8. Alexakis A., Bckvall J. E., Krause N., Pmies O., Diguez M., Chem. Rev., 108, 2796-2823 (2008).
9. Harutyunyan S. R., den Hartog T., Geurts K., Minnaard A. J., Feringa B. L., Chem. Rev., 108, 2824-2852 (2008).
10. Our Recent Example: Matsumoto Y., Yamada K., Tomioka K., J. Org. Chem., 73, 4578-4581 (2008).
11. Review: Hayashi T., Yamasaki K., Chem. Rev., 103, 2829-2844 (2003).
12. Takaya Y., Ogasawara M., Hayashi T., Sakai M., Miyaura N., J. Am. Chem. Soc., 120, 5579-5580 (1998).
13. Boiteau J.-G., Imbos R., Minnaard A. J., Feringa B. L., Org. Lett., 5, 681-684 (2003).
14. Itooka R., Iguchi Y., Miyaura N., J. Org. Chem., 68, 6000-6004 (2003).
15. Shintani R., Tokunaga N., Doi H., Hayashi T., J. Am. Chem. Soc., 126, 6240-6241 (2004).
16. Shintani R., Duan W.-L., Nagano T., Okada A., Hayashi T., Angew. Chem., Int. Ed., 44, 4611-4614 (2005).
17. Imamoto T., Sugita K., Yoshida K., J. Am. Chem. Soc., 127, 11934-11935 (2005).
18. Okamoto K., Hayashi T., Rawal V. H., Org. Lett., 10, 4387-4389 (2008).
19. Kanai M., Koga K., Tomioka K., Tetrahedron Lett., 33, 7193-7196 (1992).
20. Kanai M., Tomioka K., Tetrahedron Lett., 36, 4273-4274 (1995).
21. Kanai M., Nakagawa Y., Tomioka K., Tetrahedron, 55, 3843-3854 (1999).
22. Mori T., Kosaka K., Nakagawa Y., Nagaoka Y., Tomioka K., Tetrahedron: Asymmetry, 9, 3175-3178 (1998).
23. Soeta T., Kuriyama M., Tomioka K., J. Org. Chem., 70, 297-300 (2005).
24. Soeta T., Selim K., Kuriyama M., Tomioka K., Tetrahedron, 63, 6573-6576 (2007).
25. Soeta T., Selim K., Kuriyama M., Tomioka K., Adv. Synth. Catal., 349, 629-635 (2007).
26. Selim K., Soeta T., Yamada K., Tomioka K., Chem. Asian J., 3, 342-350 (2008).
27. Kuriyama M., Tomioka K., Tetrahedron Lett., 42, 921-923 (2001).
28. Kuriyama M., Nagai K., Yamada K., Miwa Y., Taga T., Tomioka K., J. Am. Chem. Soc., 124, 8932-8939 (2002).
29. Chen Q., Kuriyama M., Soeta T., Hao X., Yamada K., Tomioka K., Org. Lett., 7, 4439-4441 (2005).
30. Chen Q., Soeta T., Kuriyama K., Yamada K., Tomioka K., Adv. Synth. Catal., 348, 2604-2608 (2006).
31. Srgel S., Tokunaga N., Sasaki K., Okamoto K., Hayashi T., Org. Lett., 10, 589-592 (2008).
32. Sakuma S., Sakai M., Itooka R., Miyaura N., J. Org. Chem., 65, 5951-5955 (2000).
33. The first "a" and second "a" of 8aa are derived from the suffixes of 7a and 5a, respectively.
34. Kuriyama M., Soeta T., Hao X., Chen Q., Tomioka K., J. Am. Chem. Soc., 126, 8128-8129 (2004).
35. Defieber C., Paquin J. F., Serna S., Carreira E. M., Org. Lett., 6, 3873-3876 (2004).
36. Hubertus A., Horst S., Chem. Ber., 123, 829-836 (1990).
37. Nudelman N. S., Garcia G. V., J. Org. Chem., 66, 1387-1394 (2001).
38. Leitereg T. J., Cram D. J., J. Am. Chem. Soc., 90, 4011-4018 (1968).