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Synfacts 2008(4): 0423-0423  
DOI: 10.1055/s-2008-1042833
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Primary Amine Catalyzed Aldolization

Contributor(s): Benjamin List, Lars Ratjen
S. Luo*, H. Xu, L. Zhang, J. Li, J.-P. Cheng*
Institute of Chemistry and Graduate School, Chinese Academy of Sciences, Beijing and Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

A highly diastereo- and enantio­selective direct aldol reaction mediated by primary amine catalyst 1 in combination with TfOH and 3-nitrobenzoic acid as additives is reported. The addition of acyclic hydroxyketones to various aromatic aldehydes led to the formation of syn-products 2. In contrast, protected dihydroxyacetone 3 gave the analogous anti-products 4. The authors explain the observed diastereoselectivity with transition states 2a and 4a, implying Z-or E-enamines, respectively.