Asymmetric Aldol Reaction in Water Catalyzed by Chitosan
Aerogel

doi:10.1055/s-0030-1258917

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Synfacts 2010(12): 1438-1438
DOI: 10.1055/s-0030-1258917

Polymer-Supported Synthesis

Asymmetric Aldol Reaction in Water Catalyzed by Chitosan Aerogel

Contributor(s): Yasuhiro Uozumi, Aya Tazawa
A. Ricci*, L. Bernardi, C. Gioia, S. Vierucci, M. Robitzer, F. Quignard*
University of Bologna, Italy; Institut Charles Gerhardt-Montpellier, France

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Publication History

Publication Date:
22 November 2010 (online)

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Significance

Aerogel microspheres of chitosan catalyzed the direct aldol reaction of para-nitrobenzaldehyde (1) or isatin (2) with ketones in water to afford the corresponding products 3 or 4 in 76-97% yield with up to 93% ee. When 2,4-dinitrophenol (DNP) or stearic acid was used as an additive, the enantiomeric excess of 3c was increased (DNP; anti/syn = 76:24, 92% ee for the anti product, stearic acid; anti/syn = 76:24, 93% ee for the anti product).