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Synfacts 2009(4): 0461-0461  
DOI: 10.1055/s-0028-1087855
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Dendritic Effect of Supported Proline-Based Catalysts for Aldol Reaction

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
K. Goren, T. Kehat, M. Portnoy*
Tel Aviv University, Israel
Elucidation of Architectural Requirements from a Spacer in Supported Proline-Based Catalysts of Enantioselective Aldol Reaction
Adv. Synth. Catal.  2009,  351:  59-65  
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Publication History

Publication Date:
23 March 2009 (online)

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Key words

polymer-supported prolines - organocatalysis - dendrimers - aldol reaction

Significance

The dendritic effect of polystyrene-supported proline analogues as heterogeneous organocatalysts for asymmetric aldol reaction was described. Analogues of the G2-catalytic dendron were prepared and used for the aldol reaction of benzaldehyde (R = H, NO2) with acetone (27 equiv). The fully dendritic G2(Pro) gave the higher yield (94%) and enantioselectivity (84%).

Comment

The authors previously observed that the introduction of a short dendritic spacer between the polymer core and the 4-hydroxyproline-derived catalytic units provided a more active and enantioselective catalyst as compared to the spacer-less non-dendritic analogue (Chem. Commun. 2007, 2823).

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