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
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
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3-(1s)-1,2-dihydroxyethyl-1,5-dihydro-3h-2,4-benzodioxepine : (1,2-ethanediol, 1-(1,5-dihydro-2,4-benzodioxepin-3-yl)-, (s)-)
Ryu Oi,K. B. Sharpless +1 more
Journal ArticleDOI
Synthesis of a Bifunctional Ligand for the Sequential Enantioselective Catalysis of Various Reactions
TL;DR: A new bifunctional ligand capable of promoting various enantioselective catalytic transformations has been prepared by connecting a bis(oxazoline) to dihydroquinidine via a spacer, employed in a one-pot procedure.
Journal ArticleDOI
Asymmetric dihydroxylations of 1-substituted (E)- and (Z)-3-methylpent-2-en-4-ynes: full compliance with the Sharpless mnemonic re-established and embellished.
TL;DR: The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.
Journal ArticleDOI
Isotopic Labeling for Determination of Enantiomeric Purity by 2H NMR Spectroscopy
TL;DR: The use of 2H NMR spectroscopy as a tool for the analysis of enantiomeric purity is reported and assays allow for simple semiquantitative analysis of asymmetric transformations.
Journal ArticleDOI
Silica-supported chitosan–osmium tetroxide complex catalyzed vicinal hydroxylation of olefins using hexacyanoferrate(III) ion as a cooxidant
TL;DR: SiO2-CS-OsO4 has been found to be able to catalyze the dihydroxylation of styrene, α-methyl-styrene, 1-heptene,1-octene and 1-decene.
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.