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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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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An expedient approach to the diphenyl ether cross-linked amino acids of glycopeptide antibiotics
TL;DR: Displacement reactions of 2,6-dibromobenzoquinone with phenoxides and subsequent elaboration of 5 into the aryl amino acid of model C,D,E-ring segment of vancomycin have been described.
Journal ArticleDOI
A new route to isodityrosine-derived cyclic peptides: Application to K-13
TL;DR: A versatile approach suitable for isodityrosine derived cyclic peptides, and its application to K-13 have been described.
Reference EntryDOI
Epoxide Migration (Payne Rearrangement) and Related Reactions
TL;DR: A comprehensive review of epoxide migration, including factors influencing the equilibrium position, conditions leading to in situ epoxide opening, and examples of electrophilic trapping can be found in this paper.
Journal ArticleDOI
Absolute stereochemistry of TT-1 (rasfonin), an α-pyrone-containing natural product from a fungus, Trichurus terrophilus
TL;DR: The absolute stereochemistry of TT-1 (1=rasfonin), an α-pyrone-containing natural product from a Fungi Imperfecti, Trichurus terrophilus, was determined as 5R,6R,7S,9R, and 6′S on the basis of synthesis of diastereomers of two fragments of 1 in optically active forms, and comparison of their spectral and optical data with those of natural specimens as discussed by the authors.
Journal ArticleDOI
Synthesis of optically active secondary allylic alcohols from allylsilanes via successive asymmetric dihydroxylation (AD) and Peterson olefination reactions
Sentaro Okamoto,Sentaro Okamoto,Kousuke Tani,Kousuke Tani,Fumie Sato,Fumie Sato,K. Barry Sharpless,K. Barry Sharpless,Davit Zargarian,Davit Zargarian +9 more
TL;DR: In this article, the effects of trialkylsilyl groups on the outcome of the AD reaction on vinyl and allyl silanes are discussed, as well as their effects on the performance of allyl-silanes.
References
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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.