Stereoselective synthesis of 2-amino-1,3,5-hexane triols using l-proline catalyzed aldol reaction

An efficient synthesis of the 2-amino-1,3,5-hexane triol pattern has been achieved by a diastereoselective aldol reaction of an amino aldehyde with acetone catalyzed by l-proline.

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(S)-Benzyl 4-((R)-1-hydroxy-3-oxobutyl)-2,2-dimethyloxazolidine-3-carboxylateC17H23NO5[α]D = +5.7 (c 1, CHCl3)Source of chirality: l-serine

(S)-Benzyl 4-((1R,3R)-1,3-dihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylateC17H25NO5[α]D = −13.2 (c 1, CHCl3)Source of chirality: l-serine

Benzyl (2S,3R,5S)-1,3,5-trihydroxyhexan-2-ylcarbamateC14H21NO5[α]D = +6.6 (c 0.5, MeOH)Source of chirality: l-serine