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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Asymmetric synthesis of tetrahydrofurans by competitive [1,2]-phenylsulfanyl (PhS) migrations under thermodynamic control
TL;DR: In this paper, triols were prepared in enantiomerically enriched form by a short route that included a Sharpless asymmetric dihydroxylation; treatment of these triols with toluene-p-sulfonic acid gave THFs as thermodynamic products.
Journal ArticleDOI
Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate-phosphate rearrangement and tandem intramolecular piperidine elimination.
TL;DR: The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates, first reported compounds containing a direct P–C bond between theQuinine carbon skeleton and a phosphorus atom.
Journal ArticleDOI
Ein reagens zur bestimmung der optischen reinheit von diolen uber die bildung diastereomerer arylboronsaureester
Kevin Burgess,Alexander M. Porte +1 more
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Highly enantioselective osmium dihydroxylation of unsubstituted allyl N-phenylcarbamate using AD-mix reagents
TL;DR: In this article, a prominent effect of the phenylcarbamoyl protecting group on the asymmetric dihydroxylation (AD) reaction was confirmed in both of the reactions of allyl N-phenylcarbamate with AD-mix-α and -β, bringing about excellent enantioselectivity (>99% ee) to give (R)- and (S)-glycerol 1-(N-carbamate), respectively.
Journal ArticleDOI
Metall oder kein Metall: Das ist hier die Frage!
Michael Schwarz,Oliver Reiser +1 more
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.