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Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Uppsala University.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences. Stockholm University.
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2017 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 49, no 2, p. 383-390, article id ss-2015-z0592-opArticle in journal (Refereed) Published
Abstract [en]

An eco-friendly dual catalyst system for stereoselective aldol reactions in the presence of water is described. It is based on the cooperative action of acyclic amino acids and H-bond donating hydroxy oxime catalysts. The synthetic utility of this dual catalyst system was further demonstrated by applying it as the key step in the expeditious and highly stereoselective total synthesis of D-lyxo-phytosphingosine (29% overall yield). Here the amino acid/hydroxy oxime system significantly accelerated the direct aldol reactions in the presence of water as compared to organic solvents. The stereo-and chemoselectivity were also significantly increased.

Place, publisher, year, edition, pages
2017. Vol. 49, no 2, p. 383-390, article id ss-2015-z0592-op
Keyword [en]
aldol reaction, total synthesis, phytosphingosine, stereoselectivity, dual catalysis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-30470DOI: 10.1055/s-0036-1588089ISI: 000393232500018Scopus ID: 2-s2.0-84994573336OAI: oai:DiVA.org:miun-30470DiVA, id: diva2:1083054
Note

Financial support was provided by Mid Sweden University and the Swedish National Research Council (VR).

Available from: 2017-03-20 Created: 2017-03-20 Last updated: 2017-12-19Bibliographically approved

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Ma, GuangningPalo-Nieto, CarlosAfewerki, SamsonCordova, Armando

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