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
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Enantioselective α-Etherification of Branched Aldehydes via an Oxidative Umpolung Strategy
TL;DR: In this paper, an aminocatalytic umpolung concept that allows for the asymmetric construction of tertiary ethers in the α-position of aldehydes was proposed.
Journal ArticleDOI
Asymmetric synthesis of (−)-epi-blastmycinone and (2R,3S,4S)-3-hydroxy-4-methyl-2-(1′-n-tetradecyl)-butanolide via a tungsten-mediated cyclization reaction
TL;DR: In this article, a tungsten-mediated cyclization was used to achieve an anti-constrained synthesis of the natural lactones 1 and 2 using six or seven steps from readily available 1-trimethylsilyl-pent-1-yne.
Journal ArticleDOI
Nonracemic γ-Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ-Unsaturated Carboxylic Esters
TL;DR: In this paper, the authors focus on Sharpless' asymmetric dihydroxylation of C=C double bonds of β,γ-unsaturated carboxylic esters and show that this SAD route represents a potent easy-to-handle route to nonracemic butanolides and butenolides.
Journal ArticleDOI
Asymmetric dihydroxylation in an approach to the enantioselective synthesis of 2-arylpropanoic acid non-steroidal anti-inflammatory drugs
TL;DR: In this article, the authors introduced asymmetry into the molecules by Sharpless asymmetric dihydroxylation of the appropriate methyl styrenes, and the resultant diols were then converted into optically active epoxides and the required stereogenic center was assembled by catalytic hydrogenolysis of the introduced benzylic epoxide oxygen bond, followed by oxidation of the derived Optically active primary alcohol.
Journal ArticleDOI
Chiral polymers via asymmetric epoxidation and asymmetric dihydroxylation
TL;DR: Asymmetric epoxidation and dihydroxylation performed on suitably substituted styrene-divinylbenzene polymers yielded products which in some cases were difficult to analyze accurately as mentioned in this paper.
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.