Preparation of optically active β-carboxyaspartic acid derivatives via Pd(0)-catalyzed asymmetric substitution of Schiff base acetates

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 621-624

  O'Donnell, Martin J ^a   Zhou, Changyou ^a   Chen, Ning ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ASPARTIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029867484     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00048-1     Document Type: Article

References (15)

1. O'Donnell, M. J.; Zhou, C.; Mi, A.; Chen, N.; Kyle, J. A.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 4205.
2. O'Donnell, M. J.; Yang, X.; Li, M. Tetrahedron Lett., 1990, 31, 5135.
3. (a) BPPM: (2S,4S)-1-tert-butoxycarbonyl-4-diphenylphosphino-2-(diphenylphosphinomethyl) pyrrolidine.
4. (b) Achiwa, K. J. Am. Chem. Soc. 1976, 98, 8265;
5. (c) Baker, G. L; Fritschel, S. J.; Stille, J. R.; Stille, J. K. J. Org. Chem. 1981, 46, 2954;
6. (d) Ojima, I.; Kogure, T.; Yoda, Y. Organic Syntheses 1984, 63, 18;
7. (e) Leitner, W.; Brown, J. M.; Brunner, H. J. Am. Chem. Soc. 1993, 115, 152.
8. 4: C, 71.37; H, 6.56; N, 3.96. Found: C, 71.41; H, 6.48; N, 3.99.
9. 4, filtered, evaporated and then recrystallized from hexane to give 3 (1.58 g, 90%). M.p. 103-105°C.
10. O'Donnell, M. J.; Arasappan, A.; Hornback, W. J.; Huffman, J. C. Tetrahedron Lett. 1990, 31, 157.
11. 6: C, 67.75; H, 6.40; N, 3.29. Found: C, 67.56; H, 6.33; N, 3.27.
12. 2O): 2.97 (d, J = 3.6 Hz, 2H); 4.17 (m, 2H).
13. 6: C, 72.21; H, 6.45; N, 2.72. Found: C, 72.43; H, 6.43; N: 2.78.
14. 2, 18.0]. See: (a) O'Donnell, M. J.; Bennett, W. D.; Bruder, W. A.; Jacobsen, W. N.; Knuth, K.; LeClef, B.; Polt, R. L; Bordwell, F. G.; Mrozack, S. R.; Cripe, T. A. J. Am. Chem. Soc. 1988, 110, 8520;
15. (b) Zhang, X. -M.; Bordwell, F. G. J. Phys. Org. Chem. 1994, 7, 751.