Efficient recognition-induced acceleration of a [3+2] dipolar cycloaddition reaction

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6987-6990

  Booth, Ceri A ^a   Philp, Douglas ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Azides; Cycloadditions; Kinetics; Molecular recognition

Indexed keywords

AMIDOPYRIDINE; AZIDE; CARBOXYLIC ACID; MALEIMIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR RECOGNITION; SYNTHESIS;

EID: 0032541695     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01483-X     Document Type: Article

References (12)

1. 1. For excellent general reviews, see A.J. Kirby Angew. Chem. Int. Ed. Engl. 1996, 35, 707. H. Dugas Bioorganic Chemistry - A Chemical Approach to Enzyme Action, Third Edition, Springer-Verlag, New York, 1996. For some efficient examples, see M.W. Hosseini, J.M. Lehn, K.C. Jones, K.E. Plute, K.B. Mertes, M.P. Merles J. Am. Chem. Soc. 1989, 111, 6330. I. Hue, J. Pieters, J. Rebek Jr J. Am. Chem. Soc. 1994, 116, 10296. P. Tecilla, V. Jubian, A.D. Hamilton Tetrahedron 1995, 51, 435.
2. 1. For excellent general reviews, see A.J. Kirby Angew. Chem. Int. Ed. Engl. 1996, 35, 707. H. Dugas Bioorganic Chemistry - A Chemical Approach to Enzyme Action, Third Edition, Springer-Verlag, New York, 1996. For some efficient examples, see M.W. Hosseini, J.M. Lehn, K.C. Jones, K.E. Plute, K.B. Mertes, M.P. Merles J. Am. Chem. Soc. 1989, 111, 6330. I. Hue, J. Pieters, J. Rebek Jr J. Am. Chem. Soc. 1994, 116, 10296. P. Tecilla, V. Jubian, A.D. Hamilton Tetrahedron 1995, 51, 435.
3. 1. For excellent general reviews, see A.J. Kirby Angew. Chem. Int. Ed. Engl. 1996, 35, 707. H. Dugas Bioorganic Chemistry - A Chemical Approach to Enzyme Action, Third Edition, Springer-Verlag, New York, 1996. For some efficient examples, see M.W. Hosseini, J.M. Lehn, K.C. Jones, K.E. Plute, K.B. Mertes, M.P. Merles J. Am. Chem. Soc. 1989, 111, 6330. I. Hue, J. Pieters, J. Rebek Jr J. Am. Chem. Soc. 1994, 116, 10296. P. Tecilla, V. Jubian, A.D. Hamilton Tetrahedron 1995, 51, 435.
4. 1. For excellent general reviews, see A.J. Kirby Angew. Chem. Int. Ed. Engl. 1996, 35, 707. H. Dugas Bioorganic Chemistry - A Chemical Approach to Enzyme Action, Third Edition, Springer-Verlag, New York, 1996. For some efficient examples, see M.W. Hosseini, J.M. Lehn, K.C. Jones, K.E. Plute, K.B. Mertes, M.P. Merles J. Am. Chem. Soc. 1989, 111, 6330. I. Hue, J. Pieters, J. Rebek Jr J. Am. Chem. Soc. 1994, 116, 10296. P. Tecilla, V. Jubian, A.D. Hamilton Tetrahedron 1995, 51, 435.
5. 1. For excellent general reviews, see A.J. Kirby Angew. Chem. Int. Ed. Engl. 1996, 35, 707. H. Dugas Bioorganic Chemistry - A Chemical Approach to Enzyme Action, Third Edition, Springer-Verlag, New York, 1996. For some efficient examples, see M.W. Hosseini, J.M. Lehn, K.C. Jones, K.E. Plute, K.B. Mertes, M.P. Merles J. Am. Chem. Soc. 1989, 111, 6330. I. Hue, J. Pieters, J. Rebek Jr J. Am. Chem. Soc. 1994, 116, 10296. P. Tecilla, V. Jubian, A.D. Hamilton Tetrahedron 1995, 51, 435.
6. 2. D. Philp, A. Robertson Chem. Commun. 1998, 879.
7. +.
8. 2 and may, in fact, underestimate the performance of the [1•2] complex.
9. 5. SimFit, A Program for the Analysis of Kinetic Data, Version 1.0, G. von Kiedrowski, 1994.
10. 2H] complex.
11. 4) is 1.07 M, indicating that stabilisation of the transition state leading to 3 in the [1•2] complex, rather than product stabilisation, is the dominant effect in this system.
12. 8. The Chemistry of Enzyme Action, Ed. M.I. Page, Elsevier, Amsterdam, 1984, p. 19.