Amine-catalyzed direct aldol reactions of hydroxy- and dihydroxyacetone: biomimetic synthesis of carbohydrates.
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.
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Oskar
O
Popik
Monika
M
Pasternak-Suder
Katarzyna
K
Leśniak
Magdalena
M
Jawiczuk
Marcin
M
Górecki
Jadwiga
J
Frelek
Jacek
J
Mlynarski
D000588:Amines / Q000737:chemistry*; D032701:Biomimetics; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D004098:Dihydroxyacetone / Q000737:chemistry*; D005985:Glyceraldehyde / Q000737:chemistry*; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D002241:Carbohydrates; D005985:Glyceraldehyde; D012694:Serine; D011392:Proline; D004098:Dihydroxyacetone