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
Preparation of 2(R) and 2(S) methyl-2-methylglycerates
TL;DR: In this article, both enantiomers of methyl 2,3-dihydroxy-2-methylpropanoate were prepared by a chromatographic separation of their (−)-menthyl esters followed by hydrolysis and methylation.
Journal ArticleDOI
Heteroatom-Directed Acylation of Secondary Alcohols To Assign Absolute Configuration.
TL;DR: The enantioselective acylation has now been extended to secondary alcohols bearing electron-withdrawing groups such as halides and other heteroatoms and was used to confirm the configuration of two inoterpene natural products.
Journal ArticleDOI
Asymmetric dihydroxylation of vinyl- and allyl-silanes
TL;DR: In this article, Sharpless AD-mix-α and β-reagents were used for dihydroxylation of allyl-and vinyl-silanes, and the chemical yields were typically 80% or more, but the enantiomeric excesses are critically dependent on the structure of the alkene.
Book ChapterDOI
Stereoselective synthesis of brassinosteroids
TL;DR: The brassinolide remains the main prize of synthetic endeavors and is considerably more difficult to prepare because the most readily available starting material would require the difficult operation of degrading C-28 from the side chain, or inverting the configuration of C-24, respectively.
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.