Exploiting the Curtin - Hammett Principle - Recognition-Mediated Acceleration of an Aldol Reaction

Organic Letters

Volumn 3, Issue 3, 2001, Pages 353-356

  Howell, Sarah J ^a   Ashton, Peter R ^b   Spencer, Neil ^b   Philp, Douglas ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0442327201     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006821q     Document Type: Article

References (20)

1. (a) The Chemistry of Enzyme Action; Page, M. I., Ed.; Elsevier: Amsterdam, 1984.
2. (b) Silverman, R. B. The Organic Chemistry of Enzyme-Catalyzed Reactions; Academic Press: New York, 2000.
3. (a) Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 707.
4. (b) Page, M. I. Philos. Trans. R. Soc. London, B 1991, 332, 149.
5. (a) Booth, C. A.; Philp, D. Tetrahedron Lett. 1998, 39, 6987.
6. (b) Robertson, A.; Philp, D.; Spencer, N. Tetrahedron 1999, 55, 11365.
7. (c) Bennes, R. M.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. Org. Lett. 1999, 1, 1087.
8. (a) Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678.
9. (b) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
10. (c) T. C. Bruice, Lightstone, F. C. J. Am. Chem. Soc. 1996, 118, 2595.
11. (a) Takaki, U.; Hogen Esch, T. E.; Smid. J. J. Am. Chem. Soc. 1971, 93, 6760.
12. (b) Izatt, R. M.; Terry, R. E.; Nelson, D. P.; Chan, Y.; Eatough, D. J.; Bradshaw, J. S.; Hansen, L. D.; Christensen, J. J. J. Am. Chem. Soc. 1976, 82, 7626.
13. (c) Frensdorf, H. K. J. Am. Chem. Soc. 1990, 112, 6127.
14. (a) Curtin, D. Y. Rec. Chem. Prog. 1954, 15, 111.
15. (b) Winstein, S.; Holness, N. J. J. Am. Chem. Soc. 1955, 77, 5562.
16. (c) Seeman, J. I. J. Chem. Educ. 1986, 63, 42.
17. (a) Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: Cambridge, 1991.
18. (b) Parish, W.; Stott, P.; McCausland, C.; Bradshaw, C. J. Org. Chem. 1978, 43, 4577.
19. FABMS analysis has been used previously in the study of bis(crown) complexes; see: Yamada, K.; Matsutani, S.; Uchiyama, A.; Takahashi, T. J. Inclusion Phenom. 1991, 11, 49.
20. Bradshaw, J. S.; Izatt, R. M.; Yan, Z. Chem. Rev. 1994, 94, 939.