Amine-Catalyzed Direct Aldol Reactions of Hydroxy- and Dihydroxyacetone: Biomimetic Synthesis of Carbohydrates

作者：Popik Oskar; Pasternak Soder Monika; Lesniak Katarzyna; Jawiczuk Magdalena; Gorecki Marcin; Frelek Jadwiga; Mlynarski Jacek^*

来源：Journal of Organic Chemistry, 2014, 79(12): 5728-5739.

DOI：10.1021/jo500860g

This article presents comprehensive studies on the application of primary, secondary, and tertiary amines as efficient organocatalysts for the de novo synthesis of ketoses and deoxyketoses. Mimicking the actions of aldolase enzymes, the synthesis of selected carbohydrates was accomplished in aqueous media by using proline- and serine-based organocatalysts. The presented methodology also provides direct access to unnatural L-carbohydrates from the (S)-glyceraldehyde precursor. Determination of the absolute configuration of all obtained sugars was feasible using a methodology consisting of concerted ECD and VCD spectroscopy.

• 出版日期2014-6-20