Gut, B.; Mlynarski, J.
Tertiary Amine-Promoted Asymmetric Aldol Reaction of Aldehydes
Eur. J. Org. Chem. 2015 (link to page)
The tertiary amine-catalysed direct asymmetric self-aldol reaction of various a-oxyaldehydes have been demonstrated. Using 10 mol-% of quinine catalyst, dimerization products have been formed in high yields, good anti-diastereocontrol and up to 80% ee.
Popik, O.; Pasternak-Suder, M.; Leśniak, K.; Jawiczuk, M.; Górecki, M.; Frelek, J.; Mlynarski, J.
Amine-Catalyzed Direct Aldol Reactions of Hydroxy- and Dihydroxyacetone: Biomimetic Synthesis of Carbohydrates
J. Org. Chem. 2014 79 5728-5739 (link to page)
This article presents comprehensive studies on application of primary, secondary and tertiary amines as efficient organocatalysts for the de novo synthesis of ketoses and deoxyketoses. Mimicking aldolase enzymes, synthesis of selected carbohydrates was accomplished in aqueous media by using proline- and serine-based organocatalysts. Presented methodology also provides direct access to unnatural L-carbohydrates from the (S)-glyceraldehyde precursor.
El-Sepelgy, O.; Mlynarski, J.
Biomimetic Direct Aldol Reaction of Pyruvate Esters with Chiral Aldehydes
Adv. Synth. Catal. 2013 355 281-286 (link to page)
Direct aldol reactions of pyruvate esters with sugar aldehydes is efficiently promoted by dinuclear metal complexes or chiral chinchona alkaloid organocatalysts. Application of sterically hindered aryl esters allows the to-date problematic aldol reaction of pyruvate donors with controlled syn- or anti-selectivity en route to the short and efficient synthesis of 3-deoxy-2-ulosonic acids.