Catalytic asymmetric allylation of prochiral nucleophiles, α-acetamido- β-ketoesters [10]

Journal of the American Chemical Society

Volumn 121, Issue 13, 1999, Pages 3236-3237

  Kuwano, Ryoichi ^a   Ito, Yoshihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ACETAMIDO BETA KETOESTER; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LETTER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033531681     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9900104     Document Type: Letter

References (42)

1. For reviews, see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365.
2. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
3. Williams, J. M. J. Synlett 1996, 705-710.
4. Lübbers, T.; Metz, P. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 4, pp 2371-2473.
5. For recent examples, see: (a) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364.
6. (b) von Matt, P.; Pfalz, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 566-568.
7. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
8. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 3047-3050.
9. (a) Fiaud, J.-C.; De Gournay, A. H.; Lachevéque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175-185.
10. (b) Hayashi, T.; Kanehira, K.; Tsuchiya, H.; Kumada, M. J. Chem. Soc., Chem. Commun. 1982, 1162-1164.
11. Ito, Y.; Sawamura, M.; Matsuoka, M.; Matsumoto, Y.; Hayashi, T. Tetrahedron Lett. 1987, 28, 4849-4852.
12. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113-120.
13. (e) Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 2586-2592.
14. (f) Sawamura, M.; Nakayama, Y.; Tang, W.-M.; Ito, Y. J. Org. Chem. 1996, 61, 9090-9096.
15. (g) Genet, J.-P.; Ferroud, D.; Juge, S.; Montes, J. R. Tetrahedron Lett. 1986, 27, 4573-4576.
16. (h) Genet, J.-P.; Juge, S.; Montes, J. R.; Gaudin, J. M. J. Chem. Soc., Chem. Commun. 1988, 718-719.
17. Genet. J.-P.; Juge, S.; Achi, S.; Mallart, S.; Montes, J. R.; Levif, G. Tetrahedron 1988, 44, 5263-5275.
18. (a) Baldwin, I. C.; Williams, J. M. J. Tetrahedron: Asymmetry 1995, 6, 679-682.
19. (b) Trost, B. M.; Ariza, X. Angew. Chem., Int. Ed. Engl. 1997, 36, 2635-2637.
20. (a) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416-3426.
21. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Chem. Soc., Chem. Commun. 1984, 107-108.
22. Hayashi, T.; Yamamoto, A.; Ito, Y. J. Organomet. Chem. 1988, 338, 261-264.
23. Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309-3310.
24. Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997, 119, 7879-7880.
25. For catalytic asymmetric syntheses of α-alkylated α-amino acids with high enantiomeric excess, see: (a) Ito, Y.; Sawamura, M.; Shirakawa, E.; Hayashizaki, K.; Hayashi, T. Tetrahedron 1988, 44, 5253-5262.
26. (b) Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 11532-11533 and ref 4b.
27. (R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl: Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
28. Representative results with other chiral ligands in THF were as follows: (+)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)-butane (DIOP: 2% ee), (2S,3S)-2,3-bis(diphenylphosphino)butane (CHIRAPHOS: 1% ee), (R)-N,N-dimethyl-1-[(S)-1′,2-bis(diphenylphosphino)ferrocenyl]-ethylamine (BPPFA: 13% ee), (R,R)-2,2″-bis[(S)-1-(diphenylphosphino)ethyl]-1,1″-biferrocene (PhTRAP: 21% ee), (1R,2R)-bis[N-(2′-dipbenylphosphino)-benzoylamino]cyclohexane (no reaction), (S)-2-[2-(diphenylphosphino)phenyl]-4-(phenyl)oxazoline (1% ee).
29. 2 (31% ee), i-PrOH (40% ee).
30. (a) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730-4743.
31. (b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046-2054.
32. Hayashi, T.; Yamamoto, A.; Hagihara, T. J. Org. Chem. 1986, 51, 723-727.
33. For crystal structures of BINAP-palladium complexes with a di- or trisubstituted π-allyl ligand, see: (a) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83-90.
34. (b) Pregosin, P. S.; Rüegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 5040-5048.
35. Drommi, D.; Nesper, R.; Pregosin, P. S.; Trabesinger, G.; Zürcher, F. Organometallics 1997, 16, 4268-4275.
36. Yamaguchi, M.; Yabuki, M.; Yamagishi, T.; Sakai, K.; Tsuhomura, T. Chem. Lett. 1996, 241-242.
37. Equatorial orientation of phenyl group in BINAP-metal complex was defined in the following references: (a) Noyori, R. Science 1990, 248, 1194-1199.
38. (b) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196.
39. Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159-7161.
40. The relative stereochemisty between the 2- and 3-position was determined by the X-ray crystal structure of racemic 5 (R = H). See Supporting Information.
41. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
42. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.