Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Mid Sweden University, Sweden.
Show others and affiliations
Number of Authors: 5
2017 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 49, no 2, 383-390 p.Article 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, 383-390 p.
Keyword [en]
aldol reaction, total synthesis, phytosphingosine, stereoselectivity, dual catalysis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-141303DOI: 10.1055/s-0036-1588089ISI: 000393232500018OAI: oai:DiVA.org:su-141303DiVA: diva2:1086843
Available from: 2017-04-04 Created: 2017-04-04 Last updated: 2017-04-04Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text
By organisation
Department of Materials and Environmental Chemistry (MMK)Department of Organic Chemistry
In the same journal
Synthesis (Stuttgart)
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 511 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf