Hemiacetals in dynamic covalent chemistry: Formation, exchange, selection, and modulation processes

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8428-8432

  Drahoňovský, Dušan ^a   Lehn, Jean Marie ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DISPLAY COMPONENTS; DYNAMIC COVALENT CHEMISTRY; FAST RESPONSE; HEMIACETALS; METAL CATION; REVERSIBLE FORMATION;

CHEMICAL REACTIONS;

DYNAMIC RESPONSE;

ALCOHOL; ALDEHYDE; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; LEAD; METAL ION; ZINC ION;

ARTICLE; MOLECULAR DYNAMICS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 70350712183     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9009886     Document Type: Article

References (10)

1. Lehn, J.-M. Chem. Soc. Rev. 2007, 36, 151.
2. (a) Rowan, S. J.; Canrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898.
3. (b) Corbett, P. T.; Leclaire, J.; Vial, L.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652.
4. (c) Ladame, S. Org. Biomol. Chem. 2008, 6, 219.
5. Lehn, J.-M. Chem. - Eur. J. 1999, 5, 2455.
6. Acetals undergo acid-catalyzed exchange of carbonyl and alcohol components and have been used for generation of dynamic combinatorial libraries; see: (a) Berkovic-Berger, D.; Lemcoff, N. G. Chem. Commun. 2008, 1686.
7. (b) Fuchs, B.; Nelson, A.; Star, A.; Stoddart, J. F.; Vidal, S. Angew. Chem., Int. Ed. 2003, 42, 4220.
8. (c) Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. J. Am. Chem. Soc. 2005, 127, 13666.
9. (d) For a very recent reference on hemiacetals, see: Soutullo, M. D.; O'Brien, R. A.; Gaines, K. E.; Davis, J. H., Jr. Chem. Commun. 2009, 2529.
10. Hemiaminals are labile intermediates in imine formation and their use in DCC has been explored recently. They may be stabilized by a synthetic receptor; see: Iwasawa, T.; Hooley, R. J.; Rebek, J. Science 2007, 317, 493.