Reactivity and Molecular Recognition: Amine Methylation by an Introverted Ester

Journal of the American Chemical Society

Volumn 125, Issue 48, 2003, Pages 14682-14683

  Purse, Byron W ^a   Ballester, Pablo ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ESTER DERIVATIVE;

ALKYLATION; ARTICLE; BINDING SITE; ENVIRONMENTAL TEMPERATURE; HALF LIFE TIME; METHYLATION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETER;

AMINES; ESTERS; ETHERS, CYCLIC; METHYLATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RESORCINOLS; THERMODYNAMICS;

EID: 0345724829     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036595q     Document Type: Article

References (14)

1. (a) Willstätter, R. Ber. 1902, 35, 584.
2. (b) Willstätter, R.; Kahn, W. Ber. 1902, 35, 2757.
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5. Eliel, E. L.; Anderson, R. P. J. Am. Chem. Soc. 1952, 74, 547.
6. Pierce, A. C.; Joullié, M. M. J. Org. Chem. 1962, 27, 3968.
7. Zaugg, H. E.; Helgren, P. F.; Schaefer, A. D. J. Org. Chem. 1963, 28, 2617.
8. Ballester, P.; Tadayoni, B. M.; Branda, N.; Rebek, J., Jr. J. Am. Chem. Soc. 1990, 112, 3685.
9. Renslo, A. R.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2000, 39, 3281.
10. Wash, P. L.; Renslo, A. R.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2001, 40, 1221 and references therein.
11. -1 for the reaction of pyrrolidine with methyl 2,3-dihydro-3-phenyl-3-benzofurancarboxylate; the reaction mixture (at molar concentration) must be heated at 90 °C for hours to reach completion.6
12. Determined using the GRASP program. Nicholls, A.; Sharp, K.; Honig, B. Proteins 1991, 11, 281.
13. See, for example: Regan, C. K.; Craig, S. L.; Brauman, J. I. Science 2002, 295, 2245.
14. 4 fold. When comparing the reactions of 1b and 2b with quinuclidine, the acceleration is even greater.