Amine-Catalyzed Cascade Reactions of Unprotected AldosesAn Operationally Simple Access to Defined Configured Stereotetrads or Stereopentads

An amine-catalyzed cascade reaction of unprotected carbohydrates with 1.3-diketones was elaborated. This cascade is based on a Knoevenagel reaction/intramolecular ketalization/retro-aldol reaction. By application of this operationally simple protocol, a direct access to optically active stereopentad...

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Published inACS catalysis Vol. 6; no. 8; pp. 5549 - 5552
Main Authors Richter, Celin, Krumrey, Michael, Bahri, Marwa, Trunschke, Sebastian, Mahrwald, Rainer
Format Journal Article
LanguageEnglish
Published American Chemical Society 05.08.2016
Subjects
carbohydrates
cascade reactions
amine-catalysis
stereoselectivity
chiral stereopentads
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Summary:An amine-catalyzed cascade reaction of unprotected carbohydrates with 1.3-diketones was elaborated. This cascade is based on a Knoevenagel reaction/intramolecular ketalization/retro-aldol reaction. By application of this operationally simple protocol, a direct access to optically active stereopentads or stereotetrads is given. Rules of configurative outcomes will be discussed.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.6b01699