Rhodium-catalyzed asymmetric hydrogenation through dynamic kinetic resolution: asymmetric synthesis of anti-β-hydroxy-α-amino acid esters

Tetrahedron Asymmetry

Volumn 17, Issue 4, 2006, Pages 481-485

  Makino, Kazuishi ^a   Fujii, Takefumi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AMINO ACID DERIVATIVE; HYDROGEN; RHODIUM;

AMINO ACID SYNTHESIS; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; HYDROGENATION; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 33645884740     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.01.040     Document Type: Article

References (19)

1. For reviews, see:. Ohkuma T., Kitamura M., and Noyori R. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH 1-110
2. Chi Y., Tang W., and Zhang X. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH 1-31
3. Halpern J. Science 217 (1982) 401-407
4. Halpern J. In: Morrison J.D. (Ed). Chiral Catalysis. Asymmetric Synthesis Vol. 5 (1985), Academic Press 41-69
5. For reviews on dynamic kinetic resolution, see:. Noyori R., Tokunaga M., and Kitamura M. Bull. Chem. Soc. Jpn. 68 (1995) 36-56
6. Ward R.S. Tetrahedron: Asymmetry 6 (1995) 1475-1490
7. Pellissier H. Tetrahedron 59 (2003) 8291-8327
8. Noyori R., Ikeda T., Ohkuma T., Widhalm M., Kitamura M., Takaya H., Akutagawa S., Sayo N., Saito T., Taketomi T., and Kumobayashi H. J. Am. Chem. Soc. 111 (1989) 9134-9135
9. Makino K., Goto T., Hiroki Y., and Hamada Y. Angew. Chem., Int. Ed. 43 (2004) 882-884
10. Hamada, Y.; Makino, K. World Patent WO2005/005371 A1, 2005.
11. Makino K., Hiroki Y., and Hamada Y. J. Am. Chem. Soc. 127 (2005) 5784-5785
12. Ishizumi, K.; Terashima, T.; Kojima, A. Jpn. Kokai Tokkyo Koho, Jpn. H02-172956, 1990.
13. Genet J.P., Pinel C., Mallart S., Juge S., Thorimbert S., and Laffitte J.A. Tetrahedron: Asymmetry 2 (1991) 555-567
14. Hara O., Ito M., and Hamada Y. Tetrahedron Lett. 39 (1998) 5537-5540
15. Togni A., Breutel C., Schnyder A., Spindler F., Landert H., and Tijiani A. J. Am. Chem. Soc. 116 (1994) 4062
16. Togni A. Angew. Chem., Int. Ed. 35 (1996) 1475
17. 1H NMR spectrum and the enantiomeric excess was determined by HPLC.
18. Compound 8 was prepared from (S)-alanine methyl ester hydrochloride in four steps: (1) formation of alanine methyl ester benzophenone imine by exchange reaction with benzophenone imine, (2) C-benzoylation of the benzophenone imine with benzoyl chloride in the presence of potassium tert-butoxide at 23 °C in THF and subsequent treatment with 3 M hydrochloric acid, (3) N-protection of the resulting 2-methyl-alanine methyl ester for purification with di-tert-butyldicarbonate in the presence of triethylamine in THF, (4) N-deprotection with 4 M HCl-dioxane.
19. 3) δ 1.21 (d, J = 6.0 Hz, 3H), 3.77 (s, 3H), 4.90 (s, 3H), 7.30-7.35 (m, 5H), see (a) Schöllkopf, U.; Groth, U.; Hartwig, W. Liebigs Ann. Chem. 1981, 2407-2418; (b) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. Tetrahedron: Asymmetry 2000, 11, 2195-2204. The enantiomeric excess of 9 was determined to be 96% ee by HPLC analysis of the N-Bz derivative using Daicel Chiralcel AD (0.46 ∅ × 25 cm, n-hexane/2-PrOH = 85:15, flow 0.5 mL/min): (2S,3R)-isomer, 28.3 min (minor), (2R,3S)-isomer, 31.9 min (major).