An efficient biomimetic C3+Cn entry to amino sugars and derivatives via a direct asymmetric organocatalytic Mannich methodology employing 2,2-dimethyl-1,3-dioxan-5-one as a dihydroxyacetone phosphate equivalent and N-PMP or N-Boc protected imines has been developed. The Mannich bases were obtained in high diastereo- and enantiomeric excesses (78% to >99% de, 81-98% ee) and were further elaborated using diastereoselective reduction protocols, as well as via diastereoselective direct reductive amination reactions.
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Enders et al. (2006) studied this question.