A straightforward entry into enantiomerically enriched β-amino-α- hydroxyphosphonic acid derivatives

Tetrahedron Asymmetry

Volumn 9, Issue 5, 1998, Pages 745-748

  Cravotto, Giancarlo ^a   Giovenzana, Giovanni B ^b   Pagliarin, Roberto ^b   Palmisano, Giovanni ^a   Sisti, Massimo ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b Dipto di Chim Organ e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; PSEUDOPEPTIDE; VINYL DERIVATIVE;

ENANTIOMER; HYDROLYSIS; HYDROXYLATION; PRIORITY JOURNAL; REVIEW;

EID: 0032513064     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00038-X     Document Type: Article

References (22)

1. 1. (a) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587;
2. (b) ibid. 1990, 31, 5591;
3. (c) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W. J. Med. Chem. 1995, 38, 4557.
4. 2. Stowasser, B.; Budt, K.-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
5. 3. Yokomatsu, T.; Yoshida, Y.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1401.
6. 4. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451;
7. (b) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 30, 649.
8. 5. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
9. 6. Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365.
10. 7. Lohray, B. B.; Maji, D. K.; Nandanan, B. Indian J. Chem. 1995, 34B, 1023.
11. 8. Mikolajczych, M.; Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976, 396.
12. 9. Bentrude, W. G.; Setzer, W. N. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, Verkade, E. J. G.; Quin, L. D., Ed.; VCH: FL, 1987, pp. 365-389.
13. H-H (<2.5 Hz) of the corresponding trans-isomer (Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fuji, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999).
14. 11. For the stereo selection rules, see: Johnson, R. A.; Sharpless, K. B., Catalytic Asymmetric Dihydroxylation, In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, Germany, 1993, pp. 227-272.
15. 4P: C 44.25%, H 5.57%, N 6.45%.
16. 13. Burger, A., Isosterism and Bioisosterism in Drug Design, Prog. Drug Res. 1991, 37, 287.
17. 14. Georg, G. I.; Harriman, G. C. B.; Vander Velde, D. G.; Boge, T. C.; Cheruvallath, Z. S.; Datta, A.; Hepperle, M.; Park, H.; Holmes, R. H.; Jayasinghe, L., Medicinal Chemistry of Paclitaxel: Chemistry, Structure-Activity Relationships and Conformational Analysis, In Taxane Anticancer Agents: Basic Science and Current Status; Georg, G. I.; Chen, T. T.; Ojima, I.; Vyas, D. M., Eds.; ACS Symposium Series 583; ACS: Washington, DC, 1995, pp. 217-232.
18. 15. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1, 1975, 1574;
19. (b) Hartwig, W. Tetrahedron, 1983, 39, 2609;
20. (c) Prudhomme, D. R.; Wang, Z.; Rizzo, C. J. J. Org. Chem. 1997, 62, 8257 and references cited therein.
21. 16. This work was taken in part from: Vacca, M. Test di Laurea, Università di Milano, November 1997. After completion of this manuscript we became aware of a preliminary communication by Thomas and Sharpless (Thomas, A. A.; Sharpless, K. B., Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA, Apr 13-17, 1997; American Chemical Society, Washington, DC, 1997; ORGN 126).
22. 16. This work was taken in part from: Vacca, M. Test di Laurea, Università di Milano, November 1997. After completion of this manuscript we became aware of a preliminary communication by Thomas and Sharpless (Thomas, A. A.; Sharpless, K. B., Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA, Apr 13-17, 1997; American Chemical Society, Washington, DC, 1997; ORGN 126).