Intramolecular nucleophilic catalysis and the exceptional reactivity of N-benzyloxycarbonyl α-aminophosphonochloridates

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 9, 2002, Pages 1538-1543

  Cullis, Paul M ^a   Harger, Martin J P ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DERIVATIVES; HYDROGEN BONDS; HYDROLYSIS; METHANOL; ORGANIC ACIDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

INTRAMOLECULAR NUCLEOPHILIC CATALYSIS;

AROMATIC HYDROCARBONS;

EID: 0036025632     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b204935j     Document Type: Article

References (24)

1. P. Kafarski, B. Lejczak Phosphorus, Sulfur Silicon Relat. Elem. 1991 63 193.
2. J. Huang, R. Chen Heteroat. Chem. 2000 11 480.
3. V. P. Kukhar and H. R. Hudson Aminophosphonic and Aminophosphinic Acids, Wiley, Chichester, 2000.
4. R. Hirschmann, K. M. Yager, C. M. Taylor, J. Witherington, P. A. Sprengeler, B. W. Phillips, W. Moore, A. B. Smith, III J. Am. Chem. Soc. 1997 119 8177.
5. J. Rahil, R. F. Pratt J. Chem. Soc., Perkin Trans. 2 1991 947.
6. R. Kluger, J. L. W. Chan J. Am. Chem. Soc. 1976 98 4913.
7. R. Kluger, J. F. Chow, J. J. Croke J. Am. Chem. Soc. 1984 106 4017.
8. L. A. Reiter, B. P. Jones J. Org. Chem. 1997 62 2808.
9. R. A. Naylor, A. Williams J. Chem. Soc., Perkin Trans. 2 1976 1908.
10. A. B. Smith, III, L. Ducry, R. M. Corbett, R. Hirschmann Org. Lett. 2000 2 3887.
11. P. M. Cullis, M. J. P. Harger Chem. Commun. 2002 458.
12. N. A. Jacobsen, P. A. Bartlett J. Am. Chem. Soc. 1981 103 654.
13. K. A. Petrov, V. A. Chauzov, I. V. Pastukhova, N. N. Bogdanov J. Gen. Chem. USSR (Engl. Transl.) 1976 46 1226.
14. M. J. P. Harger, A. Williams J. Chem. Soc., Perkin Trans. 1 1986 1681.
15. R. S. Edmundson Chemistry of Organophosphorus Compounds, ed. F. R. Hartley Wiley, Chichester 1996, vol. 4, ch. 6.
16. A. A. Neimysheva and I. L. Knunyants J. Gen. Chem. USSR (Engl. Transl.), 1968, 38, 575.
17. I. L. Knunyants, A. A. Neimysheva J. Gen. Chem. USSR (Engl. Transl.) 1972 42 2415.
18. M. J. P. Harger, A. Williams J. Chem. Soc., Perkin Trans. 1 1989 563.
19. B. Capon and S. P. McManus Neighbouring Group Participation, Plenum, New York, 1976, vol. 1, ch. 2.
20. E. L. Eliel and S. H. Wilen Stereochemistry of Carbon Compounds, Wiley, New York, 1994, pp. 682–684.
21. I. V. Blagoeva, D. T. Tashev, A. J. Kirby J. Chem. Soc., Perkin Trans. 1 1989 1157.
22. R. F. Brown, N. M. van Gulick J. Org. Chem. 1956 21 1046.
23. E. L. Eliel, D. E. Knox J. Am. Chem. Soc. 1985 107 2946.
24. M. Bodanszky Principles of Peptide Synthesis, Springer-Verlag, Berlin, 1984, pp. 10–11.