Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water
2017 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 49, no 2, 383-390 p.Article in journal (Refereed) Published
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, 383-390 p.
aldol reaction, total synthesis, phytosphingosine, stereoselectivity, dual catalysis
IdentifiersURN: urn:nbn:se:miun:diva-30470DOI: 10.1055/s-0036-1588089ISI: 000393232500018OAI: oai:DiVA.org:miun-30470DiVA: diva2:1083054
Financial support was provided by Mid Sweden University and the Swedish National Research Council (VR).2017-03-202017-03-202017-03-20Bibliographically approved