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Synfacts 2005(3): 0363-0363  
DOI: 10.1055/s-2005-921621
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Mesoporous Silica-Supported Proline Catalysis for Aldol Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
F. Calderón, R. Fernández, F. Sánchez, A. Fernández-Mayoralas*
Instituto De Química Orgánica General, Madrid, Spain
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The direct aldol reaction of hydroxyacetone with aldehydes by using an MCM-41-supported proline catalyst was developed. Thus, a reusable mesoporous silica-supported proline (MCM41-Pro, 3) was prepared from MCM-41 (1) and silylated proline derivative 2. The direct aldol reaction of isobutyraldehyde 4 (0.5 mmol) with 5 (1 mL) in the presence of 3 (20 mol%) gave anti-diol 6 in 55% yield. With the assistance of microwave (900 W), the reaction time decreased to 10 min, providing 6 in 60% yield. Five examples of the aldol reaction for various aldehydes assisted by microwaves were demonstrated (55-90% yields, 75 up to 99% ee).