Enhanced selectivities for the hydroxyl-directed methanolysis of esters using the 2-acyl-4-aminopyridine class of acyl transfer catalysts: Ketones as binding sites

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 974-978

  Sammakia, Tarek ^a   Hurley, T Brian ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINOPYRIDINE DERIVATIVE; ESTER; HYDROXYL GROUP; KETONE; PYRROLIDINE DERIVATIVE;

ARTICLE; BINDING SITE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; SYNTHESIS;

4-AMINOPYRIDINE; BINDING SITES; CATALYSIS; ESTERS; HYDROLYSIS; KETONES; KINETICS; METHANE; PYRROLIDINES;

EID: 0034712265     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991202k     Document Type: Article

References (30)

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10. For reviews on the hydration of aldehydes and ketones see: (a) Bell, R. P. In Advances in Physical Organic Chemistry; Gold, V., Ed.; Academic: New York, 1966; Vol. 4, pp 1-29. (b) Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Interscience: London, 1970; Vol. 2, pp 1-61. For a recent study, see: (c) Wiberg, K. B.; Morgan, K. M.; Malltz, H. J. Am. Chem. Soc. 1994, 116, 11067. For a study of the hydration of pyridine carboxaldehydes, see: Pocker, Y.; Meany, J. E.; Nist, B. J. J. Phys. Chem. 1967, 71, 4509. Gianni, P.; Matteoli, E. Gazz. Chim. Ital. 1975, 105, 125.
11. For reviews on the hydration of aldehydes and ketones see: (a) Bell, R. P. In Advances in Physical Organic Chemistry; Gold, V., Ed.; Academic: New York, 1966; Vol. 4, pp 1-29. (b) Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Interscience: London, 1970; Vol. 2, pp 1-61. For a recent study, see: (c) Wiberg, K. B.; Morgan, K. M.; Malltz, H. J. Am. Chem. Soc. 1994, 116, 11067. For a study of the hydration of pyridine carboxaldehydes, see: Pocker, Y.; Meany, J. E.; Nist, B. J. J. Phys. Chem. 1967, 71, 4509. Gianni, P.; Matteoli, E. Gazz. Chim. Ital. 1975, 105, 125.
12. For reviews on the hydration of aldehydes and ketones see: (a) Bell, R. P. In Advances in Physical Organic Chemistry; Gold, V., Ed.; Academic: New York, 1966; Vol. 4, pp 1-29. (b) Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Interscience: London, 1970; Vol. 2, pp 1-61. For a recent study, see: (c) Wiberg, K. B.; Morgan, K. M.; Malltz, H. J. Am. Chem. Soc. 1994, 116, 11067. For a study of the hydration of pyridine carboxaldehydes, see: Pocker, Y.; Meany, J. E.; Nist, B. J. J. Phys. Chem. 1967, 71, 4509. Gianni, P.; Matteoli, E. Gazz. Chim. Ital. 1975, 105, 125.
13. For reviews on the hydration of aldehydes and ketones see: (a) Bell, R. P. In Advances in Physical Organic Chemistry; Gold, V., Ed.; Academic: New York, 1966; Vol. 4, pp 1-29. (b) Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; Interscience: London, 1970; Vol. 2, pp 1-61. For a recent study, see: (c) Wiberg, K. B.; Morgan, K. M.; Malltz, H. J. Am. Chem. Soc. 1994, 116, 11067. For a study of the hydration of pyridine carboxaldehydes, see: Pocker, Y.; Meany, J. E.; Nist, B. J. J. Phys. Chem. 1967, 71, 4509. Gianni, P.; Matteoli, E. Gazz. Chim. Ital. 1975, 105, 125.
14. See the Supporting Information in ref 2a for the characterization of compound 14.
15. The synthesis of 6-methyl-FPP has been previously reported. See ref 2b. 6-Triethylsilyl-FPP was synthesized from 2,6-diiodo-4-(pyrrolidin-1-yl)pyridine in two steps by sequential metal halogen exchange reactions trapping with chlorotriethylsilane and then DMF.
16. The 6-triethylsilyl-FPP catalyst (15) was chosen to illustrate this point because it is the least selective of the FPP derivatives we have prepared, displaying the largest rate of the nondirected reaction. Due to the high rate of this reaction, a delay in the methanolysis of 12 would be most evident with this catalyst.
17. No reaction is observed between benzaldehyde and bromoethanol.
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