Abstract
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.
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