Heterocycles with a Stereogenic Phosphorus or Sulfur Atom Derived from Aminoalcohols or Aminonaphthols

Krasowska, Dorota; Chrzanowski, Jacek; Drabowicz, J.

doi:10.1016/bs.aihch.2015.08.002

Cited by 5 publications

(1 citation statement)

References 175 publications

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“…Five‐membered heterocycles1 with a stereogenic phosphorus atom are broadly applicable in stereoselective syntheses of compounds involved in biopharmaceutical drug design efforts 2. As potential therapeutic agents, oligodeoxyribonucleotide phosphorothioates (PS‐ODNs)3 and PS‐nucleotides4 require improved synthetic availability, hopefully by methods that provide defined chirality on the P ‐centre.…”

Section: Introductionmentioning

confidence: 99%

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

Jacobsen¹

2014

ChemPhysChem

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Analysis of the kinetic energy density within a molecule identifies patterns in its electronic structure that are linked to the concept of charge-shift bonding. This is illustrated in a detailed study of twelve molecules, possessing carbon-carbon covalent as well as carbon-carbon charge-shift bonds in various degrees of orders, including propellanes and heteropropellanes. Regions of slow electrons are fundamental for such a correlation, and a RoSE (region of slow electrons) indicator ν(±), based on the positive definite kinetic energy density τ, is employed to characterize classes of charge-shift bonds in terms of its full topology of all critical points of rank three.

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Section: Introductionmentioning

confidence: 99%

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

Jacobsen¹

2014

ChemPhysChem

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Stereoselective P‐Cyclisation and Diastereoisomeric Purification of 5‐Phenyl‐3‐(pyridin‐2‐yl)‐1,3,2‐oxazaphospholidine Formed from a Thermolabile Protecting Group

2016

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A one‐pot, two‐step synthesis of 5‐phenyl‐3‐(pyridin‐2‐yl)‐1,3,2‐oxazaphospholidine from linear precursor bis(diisopropylamino){2‐[(pyridin‐2‐yl)amino]‐1‐phenylethoxy}phosphine is achieved using a stereoselective intramolecular cyclisation. Application of a pure enantiomer {1‐phenyl‐2‐[(pyridin‐2‐yl)amino]ethanol} enabled partial diastereopurification by crystallisation. For all four diastereoisomers, the absolute configuration of the P‐centre was determined using X‐ray crystallography and correlative 31P NMR data. Stereochemically pure 5a was then used in nucleoside phosphitylation reactions with partial loss of stereopurity by retention of configuration on the phosphorus centre.

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The Literature of Heterocyclic Chemistry, Part XV, 2015

Беленький

Evdokimenkova

2018

Advances in Heterocyclic Chemistry

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Heterocycles with a Stereogenic Phosphorus or Sulfur Atom Derived from Aminoalcohols or Aminonaphthols

Cited by 5 publications

References 175 publications

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

Stereoselective P‐Cyclisation and Diastereoisomeric Purification of 5‐Phenyl‐3‐(pyridin‐2‐yl)‐1,3,2‐oxazaphospholidine Formed from a Thermolabile Protecting Group

The Literature of Heterocyclic Chemistry, Part XV, 2015

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Heterocycles with a Stereogenic Phosphorus or Sulfur Atom Derived from Aminoalcohols or Aminonaphthols

Cited by 5 publications

References 175 publications

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

The Local Kinetic Energy Profile of an Inverted CarbonCarbon Bond Reveals and Refines its Charge‐Shift Character

Stereoselective P‐Cyclisation and ­Diastereoisomeric Purification of 5‐Phenyl‐3‐(pyridin‐2‐yl)‐1,3,2‐oxazaphospholidine Formed from a Thermolabile Protecting Group

The Literature of Heterocyclic Chemistry, Part XV, 2015

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Product

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About

Stereoselective P‐Cyclisation and Diastereoisomeric Purification of 5‐Phenyl‐3‐(pyridin‐2‐yl)‐1,3,2‐oxazaphospholidine Formed from a Thermolabile Protecting Group