Asymmetric addition of dialkyl phosphite and diamido phosphite anions to chiral, enantiopure sulfinimines: A new, convenient route to enantiomeric α-aminophosphonic acids

Tetrahedron Asymmetry

Volumn 8, Issue 24, 1997, Pages 3991-3994

  Mikołajczyk, Marian ^a   Lłyzwa, Piotr ^a   Drabowicz, Józef ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORAMIDIC ACID; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037831132     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00606-X     Document Type: Article

References (13)

1. P. Kafarski and P. Mastalerz, in Beiträge zur Wirkstofforschung, ed. P. Oehme, H. Löwe and E. Gores, J. Axt, Inst. f. Wirkstofforschung, Berlin, 1984, Vol. 21.
2. For a comprehensive review on the biological activity of aminophosphonic acids 1 see: P. Kafarski and B. Lejczak, Phosphorus, Sulfur and Silicon, 1991, 63, 193.
3. For comprehensive reviews, see: B. Dhawan and D. Redmore, Phosphorus and Sulfur, 1987, 32, 119; V. P. Kukhar, V. A. Soloshonok and V. A. Solodenko, Phosphorus, Sulfur and Silicon, 1994, 92, 239.
4. For comprehensive reviews, see: B. Dhawan and D. Redmore, Phosphorus and Sulfur, 1987, 32, 119; V. P. Kukhar, V. A. Soloshonok and V. A. Solodenko, Phosphorus, Sulfur and Silicon, 1994, 92, 239.
5. For recent examples of asymmetric synthesis of α-aminophosphonic acids 1, see: K. M. Yager, C. M. Taylor and A. B. Smith III, J Am. Chem. Soc., 1994, 116, 9377; H. Sasai, S. Arai, Y. Tahara and M. Shibasaki, J. Org. Chem., 1995, 60, 6656; R. Hamilton, B. Walker and B. J. Walker, Tetrahedron Lett., 1995, 36, 4451 ; A. Heisler, C. Rabiller and G. Hägele, Phosphorus, Sulfur and Silicon, 1995, 101, 273.
6. For recent examples of asymmetric synthesis of α-aminophosphonic acids 1, see: K. M. Yager, C. M. Taylor and A. B. Smith III, J Am. Chem. Soc., 1994, 116, 9377; H. Sasai, S. Arai, Y. Tahara and M. Shibasaki, J. Org. Chem., 1995, 60, 6656; R. Hamilton, B. Walker and B. J. Walker, Tetrahedron Lett., 1995, 36, 4451 ; A. Heisler, C. Rabiller and G. Hägele, Phosphorus, Sulfur and Silicon, 1995, 101, 273.
7. For recent examples of asymmetric synthesis of α-aminophosphonic acids 1, see: K. M. Yager, C. M. Taylor and A. B. Smith III, J Am. Chem. Soc., 1994, 116, 9377; H. Sasai, S. Arai, Y. Tahara and M. Shibasaki, J. Org. Chem., 1995, 60, 6656; R. Hamilton, B. Walker and B. J. Walker, Tetrahedron Lett., 1995, 36, 4451 ; A. Heisler, C. Rabiller and G. Hägele, Phosphorus, Sulfur and Silicon, 1995, 101, 273.
8. For recent examples of asymmetric synthesis of α-aminophosphonic acids 1, see: K. M. Yager, C. M. Taylor and A. B. Smith III, J Am. Chem. Soc., 1994, 116, 9377; H. Sasai, S. Arai, Y. Tahara and M. Shibasaki, J. Org. Chem., 1995, 60, 6656; R. Hamilton, B. Walker and B. J. Walker, Tetrahedron Lett., 1995, 36, 4451 ; A. Heisler, C. Rabiller and G. Hägele, Phosphorus, Sulfur and Silicon, 1995, 101, 273.
9. For recent applications of chiral sulfinimines in asymmetric synthesis, see: M. Mikołajczyk, J. Drabowicz and P. Kiełbasiński, Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis, CRC Press, Boca Raton, 1997, pp. 195-233.
10. F. A. Davis, R. E. Reddy, J. M. Szewczyk and P. S. Portonowo, Tetrahedron Lett., 1993, 34, 6229.
11. M. Mikołajczyk, P. Łyzwa, J. Drabowicz, M. W. Wieczorek and J. Błaszczyk, Chem. Commun., 1996, 1503.
12. After completion of our results we become aware of a poster presented by I. M. Lafebvre and S. A. Evans, Jr, at the ESOC-X in Basel where the asymmetric addition of sodium and lithium diethyl phosphite to (+)-(S)-2 was shown.
13. T. Głowiak, W Sawka-Dobrowolska, J. Kowalik, P. Mastalerz, M. Soroka and J. Zoń, Tetrahedron Lett., 1977, 3965.