Pd-catalyzed asymmetric allylic amination using aspartic acid derived P-chirogenic diaminophosphine oxides: DIAPHOXs

Organic Letters

Volumn 7, Issue 20, 2005, Pages 4447-4450

  Nemoto, Tetsuhiro ^a   Masuda, Takamasa ^a   Akimoto, Yuichi ^a   Fukuyama, Takashi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE MONOOXYGENASE; ASPARTIC ACID; BENZYLAMINE; BENZYLAMINE DERIVATIVE; CARBONIC ACID DERIVATIVE; OXIDE; OXYGENASE; PALLADIUM; PHOSPHINE DERIVATIVE; SOLVENT;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AMINATION; ASPARTIC ACID; BENZYLAMINES; CARBONATES; CATALYSIS; MOLECULAR STRUCTURE; OXIDES; OXYGENASES; PALLADIUM; PHOSPHINES; SOLVENTS; STEREOISOMERISM;

EID: 26444603763     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051748v     Document Type: Article

References (48)

1. For a review, see: Ohkuma, T.; Kitamura, M.; Noyori, R. Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110.
2. For recent representative examples, see: (a) Strecker reaction: Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012-10014 and references cited therein,
3. (b) Reissert reaction: Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808-11809 and references therein,
4. (c) Mannich-type reaction: Yoshida, T.; Morimoto, H.; Kumagai, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 3470-3474 and references therein.
5. (d) Boezio, A. A.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 14260-14261.
6. (e) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558-10559.
7. (f) Ogawa, C.; Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed. 2004, 43, 6491-6493.
8. (g) Ooi, T.; Kameda, M.; Taniguchi, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 9685-9694.
9. (h) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5360-5361.
10. (a) Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 16178-16179.
11. (b) Hamashima, Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861-1864 and references therein.
12. For reviews, see: (a) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
13. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2943.
14. (a) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanagi, K. J. Am. Chem. Soc. 1989, 111, 6301-6311.
15. (b) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089-4090.
16. (c) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Org. Chem. 1999, 64, 2994-2995.
17. (d) You, S.-L.; Zhu, X.-Z.; Lou, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471-7472.
18. (e) Zablocka, M.; Koprowski, M.; Donnadieu, B.; Majoral, J.-P.; Achard, M.; Buono, G. Tetrahedron Lett. 2003, 44, 2431-2415.
19. (f) Uozumi, Y.; Tanaka, H.; Shibatomi, K. Org. Lett. 2004, 6, 281-283.
20. (g) Faller, J. W.; Wilt, J. C. Org. Lett. 2005, 7, 633-636.
21. (a) Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165.
22. (b) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272-14273.
23. (c) Shu, C.; Leiner, A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2004, 43, 4797-4800.
24. (d) Tissot-Croset, K.; Polet, D.; Alexakis, A. Angew. Chem., Int. Ed. 2004, 43, 2426-2428.
25. (e) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116-117.
26. (f) Welter, C.; Dahnz, A.; Bruner, B.; Steiff, S.; Dübon, P.; Helmchen, G. Org. Lett. 2005, 7, 1239-1242.
27. (g) Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621-1624.
28. (a) Ru catalyst: Matsushima, Y.; Onitsuka, K.; Kondo, T.; Mitsudo, T.; Takahashi, S. J. Am. Chem. Soc. 2001, 123, 10405-10406.
29. (b) Ni catalyst: Bekowitz, D. B.; Maiti, G. Org. Lett. 2004, 6, 2661-2664.
30. (c) Enantiospecific allylic amination using Rh catalyst: Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761-6762.
31. (a) Nemoto, T.; Matsumoto, T.; Masuda, T.; Hitomi, T.; Hatano, K.; Hamada, Y. J. Am. Chem. Soc. 2004, 126, 3690-3691.
32. (b) Nemoto, T.; Masuda, T.; Matsumoto, T.; Hamada, Y. J. Org. Chem. 2005, 70, 7172-7178.
33. (c) Nemoto, T.; Fukuda, T.; Matsumoto, T.; Hitomi, T.; Hamada, Y. Adv. Synth. Catal. In press.
34. For representative examples of transition metal catalysis with pentavalent phosphorus preligands, see: (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513-1516.
35. (b) Jiang, X.-B.; Minnaard, A. J.; Hessen, B.; Feringa, B. L.; Duchateau, A. L. L.; Andrien, J. G. O.; Boogers, J. A. F.; de Vries, J. G. Org. Lett. 2003, 5, 1503-1506.
36. (c) Ackermann, L.; Born, R. Angew. Chem., Int. Ed. 2005, 44, 2444-2447.
37. (d) Bigeault, J.; Giordano, L.; Buono, G. Angew. Chem., Int. Ed. 2005, 44, 4753-4757 and references therein.
38. 1H NMR. This fact indicates that N-trimethylsilylated amines would be the actual nucleophiles in this reaction system. In contrast, no trimethylsilylation occurred in the case of N-methylaniline. These results appear to suggest that N-trimethylsilylation might be important for the reaction.
39. 2.
40. (a) Mori, M.; Kuroda, S.; Zhang, C.-S.; Sato, Y. J. Org. Chem. 1997, 62, 3263-3270.
41. (b) Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057-3064.
42. (c) Hamada, Y.; Sakaguchi, K.; Hatano, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297-1299.
43. (d) Mori, M.; Nakanishi, M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801-9807.
44. (e) Nishimata, T.; Sato, Y.; Mori, M. J. Org. Chem. 2004, 69, 1837-1843.
45. 3CN to palladium metal might prevent catalyst deactivation by competitive coordination of the product, resulting in the higher reactivity compared with the cases of other solvents.
46. 3CN, rt, 36 h: 57%, 35% ee]. This result indicates the importance of the 2-substituent on the asymmetric induction.
47. For the experimental procedure of asymmetric allylic amination reactions; see Supporting Information.
48. 12e