Further studies on the chemistry of piperazic acids: New building blocks for β-hydroxy-α-aminoacids through the aza-achmatowicz reaction

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 4947-4950

  Ciufolini, Marco A ^a   Shimizu, Toshio ^a   Swaminathan, Shankar ^a   Xi, Ning ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID;

ACYLATION; ARTICLE; CONFORMATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030746967     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01087-3     Document Type: Article

References (21)

1. (a) Ciufolini, M. A.; Xi, N. J. Org. Chem. 1997, 62, 2320;
2. (b) Ciufolini, M. A.; Xi, N. J. Chem. Soc., Chem. Commun. 1994, 1867;
3. (c) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685;
4. (d) Schmidt, U.; Riedl, B. Synthesis 1993, 809;
5. (e) Rebert, N. W. Dissertation, Utah State University, 1987.
6. Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Am. Chem. Soc. 1981, 103, 1241; Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243.
7. Konishi, M.; Ohkuma, H.; Sakai, F.; Tsuno, T.; Koshiyama, H.; Naito, T.; Kawaguchi, H. J. Am. Chem. Soc. 1981, 103, 1241; Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 1243.
8. Cf. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, NY, 1994; pp. 696-697 and references cited therein.
9. All calculations described here were carried out with the PC-based Hyperchem® 4.0 package, by Hypercube, Inc, Ontario, Canada.
10. Cf. Ciufolini, M. A.; Hermann, C. Y. W.; Whitmire, K. H.; Byrne, N. E. J. Am. Chem. Soc. 1989, 111, 3473, and references cited therein.
11. Xi, N. unpublished results from these laboratories.
12. Ciufolini, M. A.; Wood, C. Y. Tetrahedron Lett. 1986, 27, 5085.
13. This reagent, developed by Prof. T. Fukuyama, formerly of this Department, is especially useful for enamide formation from mixed amidals of the type 16: cf. ref. 7.
14. Luche, J. L.; Gemal, A. L. J. Chem. Soc., Chem. Commun. 1978, 976.
15. a. Klotzer, W. Synthesis 1982, 592;
16. b. Harger, M. J. P. J. Chem. Soc., Chem. Commun. 1981, 3284.
17. Cf. Curtius, T.; Zinkeisen, E. J. Prakt. Chem. 1898, 58, 310.
18. Drueckhammer. D. G.; Barbas, III, C. F.; Nozaki, K.; Wong, C. H.; Wood, C. Y., Ciufolini, M. A. J. Org. Chem. 1988, 53, 1607.
19. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185.
20. Garner, P. Tetrahedron Lett. 1984, 25, 5855.
21. 1H: 170.5, 155.5, 101.5, 97.1, 79.8, 76.8, 56.7, 56.0, 53.1, 52.5, 52.2, 35.3, 28.3.