Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols

Yagi, Kenji; Oikawa, Hideaki; Ichihara, Akitami

doi:10.1271/bbb.61.1038

Cited by 6 publications

(1 citation statement)

References 2 publications

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“…18 1 H NMR (400 MHz, CDCl 3 ): d 7.30 (m, 5H), 5.96 (dtt, J = 17.2, 6, 1.6 Hz), 5.30 (dt, J = 17.2, 1.6 Hz, 1H), 4.53 (s, 2H), 4.03 (dd, J = 6, 4.4 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ): d 138.3, 134.6, 128.4, 127.7, 127.6, 72.1, 71.1 (t, J = 1.9 Hz).…”

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity

Martı́nez

Weinstein

et al. 2013

J. Org. Chem.

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A modified protocol has been identified for Pd-catalyzed intermolecular aminoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.

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Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity

Martı́nez

Weinstein

et al. 2013

J. Org. Chem.

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Asymmetric Dihydroxylation of Alkenes

2005

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The oxidation of alkenes to vicinal diols using osmium tetroxide is one of the most selective and reliable transformations in organic synthesis. The reaction stereospecifically produces a cis‐1,2‐glycol and is tolerant of a wide array of functional groups. Methods have been developed to oxidize alkenes stoichiometrically, as well as in the presence of catalytic amounts of osmium tetroxide, when a suitable secondary oxidant is present. The latter process is particularly useful considering the expense and toxicity of osmium tetroxide. The utility of dihydroxylation in organic synthesis is enhanced by the facile transformations of the cis‐1,2‐diol products into other useful derivatives. Among the most versatile intermediates are the corresponding cyclic sulfates, which serve as reactive epoxide equivalents that can be used singly or doubly displaced with amine‐, oxygen‐, sulfur‐, or carbon‐based nucleophiles. The reaction of osmium tetroxide with alkenes is accelerated by several orders of magnitude in the presence of coordinating amine ligands such as triethylamine, quinuclidine, or diazobicyclooctane. The logical extension to asymmetric osmylation of alkenes in the presence of chiral amine bases spurred the study of asymmetric dihydroxylation. The breakthrough of catalytic turnover in the cinchona alkaloid‐osmium tetroxide system revolutionized the field of asymmetric dihydroxylation. Specialized ligands have been developed to provide position selectivity in the dihydroxylation of polyenes, efficient kinetic resolution of racemic substrates, and high levels of enantioselectivity for each of six alkene classes.

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Facile C–H bond activation for deuterium and tritium labeling of glycoconjugates conducted in ultrasonic and microwave fields: a review

Bokatzian-Johnson¹,

Maier²,

Bell³

et al. 2007

Labelled Comp Radiopharmac

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Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols

Abstract: An efficient method is described for synthesizing and four possible diastereomers of stereochemically defined monodeuterated glycerols by utilizing Sharpless asymmetric dihydroxylation.

Cited by 6 publications

References 2 publications

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity

Asymmetric Dihydroxylation of Alkenes

Facile C–H bond activation for deuterium and tritium labeling of glycoconjugates conducted in ultrasonic and microwave fields: a review

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Enantio- and Stereoselective Syntheses of Monodeuterium-labeled Glycerols

Abstract: An efficient method is described for synthesizing and four possible diastereomers of stereochemically defined monodeuterated glycerols by utilizing Sharpless asymmetric dihydroxylation.

Cited by 6 publications

References 2 publications

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)2 on Aminopalladation Stereoselectivity

Asymmetric Dihydroxylation of Alkenes

Facile C–H bond activation for deuterium and tritium labeling of glycoconjugates conducted in ultrasonic and microwave fields: a review

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Product

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Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity

Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of PhI(OAc)₂ on Aminopalladation Stereoselectivity