Journal ArticleDOI
New ligands double the scope of the catalytic asymmetric dihydroxylation of olefins
K. Barry Sharpless,Willi Amberg,Matthias Beller,Hou Chen,Jens Hartung,Yasuhiro Kawanami,Doris Lubben,Eric Manoury,Yasukazu Ogino,Tomoyuki Shibata,Tatsuzo Ukita +10 more
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TLDR
Improved ligands render terminal olefins good substrates for the osmium-catalyzed asymmetric dihydroxylation (ADH) process as discussed by the authors.Abstract:
Improved ligands render terminal olefins good substrates for the osmium-catalyzed asymmetric dihydroxylation (ADH) process, and the amounts of chiral ligand and osmium catalyst required diminish dramaticallyread more
Citations
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Journal ArticleDOI
Lipase-catalyzed enantioselective synthesis of methyl (r)- and (s)-2-tetradecyloxiranecarboxylate through sequential kinetic resolution
TL;DR: Among a variety of lipases tested, Pseudomonas fluorescens lipase has been found to induce enantioselective acylation of methyl (R,S)-2-hydroxy-2-(hydroxymethyl)hexadecanoate, affording, through sequential kinetic resolution, both enantiomers in good optical yields.
Journal ArticleDOI
Catalytic asymmetric dihydroxylation of alkenes induced by polymeric chiral ligands
TL;DR: The comparison with a soluble model compound showed that the insoluble polymer-bound ligand approach is very promising for both small- and large-scale synthesis of optically active vicinal diols.
Book ChapterDOI
9.4 – Metal Complexes as Catalysts for Oxygen, Nitrogen, and Carbon-atom Transfer Reactions
Journal ArticleDOI
An enantioselective synthesis of the A-Ring fragment of taxol
TL;DR: A-Ring fragment of taxol (2) was enantioselectively prepared by using asymmetric dihydroxylation of enol silyl ether of the parent aldehyde as discussed by the authors.
Journal ArticleDOI
(2S, 3S, 5S)- and (2S, 3S, 5R)-5-carboxaldehyde-2,3-diphenyl-1,4-dioxane as surrogates for optically pure 2,3-O-isopropylideneglyceraldehyde in asymmetric synthesis
TL;DR: In this paper, the title compounds were prepared from threo -hydrobenzoin, either enantiomer of which is readily available from trans -stilbene using the Sharpless asymmetric dihydroxylation reaction.
References
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Journal ArticleDOI
Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters
James A. Dale,Harry S. Mosher +1 more
PatentDOI
First practical method for asymmetric epoxidation
Tsutomu Katsuki,K. B. Sharpless +1 more
TL;DR: In this article, a metal alkoxide is used as a catalyst, where the metal has a coordination number of at least four, and at least one, usually two, of the alkoxide groups bonded to the metal are bonded to asymmetric carbon atoms.
Journal ArticleDOI
Asymmetric dihydroxylation via ligand-accelerated catalysis
TL;DR: Dihydroxylation asymetrique de composes ethyleniques du type styrene, vinylcyclohexane, hexene-3 en les glycols correspondants as mentioned in this paper.
Journal ArticleDOI
Asymmetric induction in the reaction of osmium tetroxide with olefins
Journal ArticleDOI
An improved synthesis of the taxol side chain and of RP 56976
TL;DR: In this paper, the methode presentee se fait au depart de phenyl-3 dihydroxy-2,3 propionate de methyle via epoxydation, et d'azoture de sodium.