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Marina Resmini Research Group

Biomimetic control of product selectivity using imprinted nanogels

The aldol reaction is one of the most important chemical tools for the formation of new C-C bonds. Organocatalysts such as proline [1], and enzymes such as aldolases [2] are important alternatives to classical chemical approaches [3] for the catalysis of this reaction and stereochemistry control.

Our group has reported the first example of molecular imprinted nanogels with aldolase type I activity and work in recent months has focussed on studies of mechanistic variations between the nanogels and the corresponding free catalyst (2S)-N-(2-pyrrolidine-2-carbonyl)-benzenesulfonamide. [4],[5]

Figure 1
Figure 1: (2S)-N-(2-pyrrolidine-2-carbonyl)-benzenesulfonamide

Preliminary data obtained by our research group has shown that the reaction between 4-NO2-benzaldehyde (1) and acetone (2) forms two main product, the aldol (3) and the condensation product (4).

Figure 2
Scheme 1: aldol condensation

The reaction between the 4-NO2-benzaldehyde and acetone was chosen as a model and the work focussed on the evaluation of product formation, in particular on the ratio of aldol (3) versus condensation (4). The obtained data provide evidence that the polymer matrix is able to influence the ratio and control formation of the side product. The results obtained with different experimental conditions will be shown and discussed.

References
1. Z. G. Hajos; D. R. Parrish, The Journal of Organic Chemistry 1974, 39, 1612-1615
2. T.D. Machajewski; C-H. Wong, Angewante Chemie International Edition 2000, 39, 1352-1374
3. S. G Nelson, Tetrahedron Asimmetry 1998, 9, 357-389
4. P. Pasetto; S.C. Maddock; M. Resmini, Analytica Chimica Acta 2005, 542, 6675
5. D. Carboni; K. Flavin; A. Servant; V. Gouverneur; M. Resmini, Chemistry: European Journal 2008, 14, 7059-7065

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